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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Mini-Review Article

Synthetic Methods of 1H-Pyrazolo[1,2-b]Phthalazine Derivatives

Author(s): Rizk E. Khidre*, Mohamed S. Mostafa, Yousef E. Mukhrish, Mounir A. Salem and Mohamed S. Behalo

Volume 26, Issue 22, 2022

Published on: 30 January, 2023

Page: [2055 - 2069] Pages: 15

DOI: 10.2174/1385272827666230124145625

Price: $65

Abstract

This review deals with the synthetic methods of pyrazolo[1,2-b]phthalazine derivatives using one-pot multi-component reactions via modern and traditional methods. The synthetic methods are subdivided into groups according to the type of reactants e.g. (1) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and acetonitriles; (2) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and aroyl acetonitriles; (3) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and acetylacetone or 4-hydroxy-2H-chromen-2-one or acetylene derivatives; (4) one-pot four-component condensation reaction of phthalimide, hydrazine hydrate, aldehydes and acetonitriles; (5) one-pot four-component reaction of phthalic acid, hydrazine hydrate, indole-3- carbaldehyde and acetonitriles; and (6) one-pot three-component condensation reaction of 2,3- dihydrophthalazine-1,4-dione, aldehyde, and dimedone derivatives. Moreover, the various methods were reported.

Keywords: Pyrazole, phthalazine, multi-component reactions, heterocycles, pharmacological activities, synthetic methods.

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[1]
Franklin, E.C. Heterocyclic nitrogen compounds. I. pentacyclic compounds. Chem. Rev., 1935, 16(3), 305-361.
[http://dx.doi.org/10.1021/cr60055a001]
[2]
Bergstrom, F.W. Heterocyclic nitrogen compounds. Part IIA. hexacyclic compounds: Pyridine, quinoline, and isoquinoline. Chem. Rev., 1944, 35(2), 77-277.
[http://dx.doi.org/10.1021/cr60111a001]
[3]
Lichtenthaler, F.W. Unsaturated O- and N-heterocycles from carbohydrate feedstocks. Acc. Chem. Res., 2002, 35(9), 728-737.
[http://dx.doi.org/10.1021/ar010071i] [PMID: 12234202]
[4]
Nabid, M.R.; Rezaei, S.J.T.; Ghahremanzadeh, R.; Bazgir, A. Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Ultrason. Sonochem., 2010, 17(1), 159-161.
[http://dx.doi.org/10.1016/j.ultsonch.2009.06.012] [PMID: 19589715]
[5]
Terrett, N.K.; Bell, A.S.; Brown, D.; Ellis, P. Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg. Med. Chem. Lett., 1996, 6(15), 1819-1824.
[http://dx.doi.org/10.1016/0960-894X(96)00323-X]
[6]
Katritzky, A.R.; Rees, C.W.; Scriven, E.F. Comprehensive Heterocyclic Chemistry II; Elsevier: Oxford, 1996, pp. 1-75.
[7]
Singh, S.K.; Reddy, P.G.; Rao, K.S.; Lohray, B.B.; Misra, P.; Rajjak, S.A.; Rao, Y.K.; Venkateswarlu, A. Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(2), 499-504.
[http://dx.doi.org/10.1016/j.bmcl.2003.10.027] [PMID: 14698190]
[8]
Genin, M.J.; Biles, C.; Keiser, B.J.; Poppe, S.M.; Swaney, S.M.; Tarpley, W.G.; Yagi, Y.; Romero, D.L. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives. J. Med. Chem., 2000, 43(5), 1034-1040.
[http://dx.doi.org/10.1021/jm990383f] [PMID: 10715167]
[9]
O’Hagan, D. Fluorine in health care: Organofluorine containing blockbuster drugs. J. Fluor. Chem., 2010, 131(11), 1071-1081.
[http://dx.doi.org/10.1016/j.jfluchem.2010.03.003]
[10]
El-Saka, S.S.; Soliman, A.H.; Imam, A.M. Synthesis, antimicrobial activity and electron impact of mass spectra of phthalazine-1, 4-dione derivatives. Afinidad, 2009, 66(540), 167. [https://raco.cat/index.php/afinidad/article/view/276782]
[11]
Zhang, L.; Guan, L.P.; Sun, X.Y.; Wei, C.X.; Chai, K.Y.; Quan, Z.S. Synthesis and anticonvulsant activity of 6-alkoxy-[1,2,4]triazolo[3,4-a]phthalazines. Chem. Biol. Drug Des., 2009, 73(3), 313-319.
[http://dx.doi.org/10.1111/j.1747-0285.2009.00776.x] [PMID: 19207467]
[12]
Ryu, C.K.; Park, R.E.; Ma, M.Y.; Nho, J.H. Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones. Bioorg. Med. Chem. Lett., 2007, 17(9), 2577-2580.
[http://dx.doi.org/10.1016/j.bmcl.2007.02.003] [PMID: 17320386]
[13]
Li, J.; Zhao, Y.F.; Yuan, X.Y.; Xu, J.X.; Gong, P. Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines. Molecules, 2006, 11(7), 574-582.
[http://dx.doi.org/10.3390/11070574] [PMID: 17971729]
[14]
Liu, D.C.; Gong, G.H.; Wei, C.X.; Jin, X.J.; Quan, Z.S. Synthesis and anti-inflammatory activity evaluation of a novel series of 6-phenoxy-[1,2,4]triazolo[3,4- a]phthalazine-3-carboxamide derivatives. Bioorg. Med. Chem. Lett., 2016, 26(6), 1576-1579.
[http://dx.doi.org/10.1016/j.bmcl.2016.02.008] [PMID: 26876930]
[15]
Gu, Y. Multicomponent reactions in unconventional solvents: state of the art. Green Chem., 2012, 14(8), 2091-2128.
[http://dx.doi.org/10.1039/c2gc35635j]
[16]
Amirmahani, N.; Mahmoodi, N.O.; Malakootian, M.; Pardakhty, A. [TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives. Mol. Divers., 2022, 26(1), 15-25.
[http://dx.doi.org/10.1007/s11030-020-10153-8] [PMID: 33150953]
[17]
Sinkkonen, J.; Ovcharenko, V.; Zelenin, K.N.; Bezhan, I.P.; Chakchir, B.A.; Al-Assar, F.; Pihlaja, K. 1H and 13C NMR study of 1-hydrazino-2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones and -1H-pyrazolo[1,2-b]phthala-zine-5,10-diones and their ring-chain tautomerism. Eur. J. Org. Chem., 2002, 2002(13), 2046-2053.
[http://dx.doi.org/10.1002/1099-0690(200207)2002:13<2046:AID-EJOC2046>3.0.CO;2-C]
[18]
Jain, R.P.; Vederas, J.C. Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase. Bioorg. Med. Chem. Lett., 2004, 14(14), 3655-3658.
[http://dx.doi.org/10.1016/j.bmcl.2004.05.021] [PMID: 15203137]
[19]
Kumar, A.; Gupta, M.K.; Kumar, M. l-Proline catalysed multicomponent synthesis of 3-amino alkylated indolesvia a Mannich-type reaction under solvent-free conditions. Green Chem., 2012, 14(2), 290-295.
[http://dx.doi.org/10.1039/C1GC16297G]
[20]
Khidre, R.E.; Radini, I.M.A.; Ameen, T.A.; Abdelgawad, A.A.M.; Triazoloquinolines, I. Synthetic methods and pharmacological properties of [1, 2, 3] triazoloquinoline derivatives. Curr. Org. Chem., 2021, 25(8), 876-893.
[http://dx.doi.org/10.2174/1385272825666210202122645]
[21]
Khidre, R.E.; Ameen, T.A.; Salem, M.A.I. Tetrazoloquinolines: synthesis, reactions, and applications. Curr. Org. Chem., 2020, 24(4), 439-464.
[http://dx.doi.org/10.2174/1385272824666200217095341]
[22]
Khidre, R.E.; Radini, I.A.M.; Ibrahim, D.A. Synthetic approaches of pyrazolyl quinolines. Mini Rev. Org. Chem., 2019, 16(4), 353-360.
[http://dx.doi.org/10.2174/1570193X15666180419142511]
[23]
Hiremath, P.B.; Kamanna, K. Microwave-accelerated facile synthesis of 1 H -pyrazolo[1,2- b]phthalazine-5,10-dione derivatives catalyzed by WEMPA. Polycycl. Aromat. Compd., 2022, 42(5), 2162-2178.
[http://dx.doi.org/10.1080/10406638.2020.1830129]
[24]
Mohamadpour, F. Catalyst-free, visible light irradiation promoted synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous ethyl lactate. J. Photochem. Photobiol. Chem., 2021, 407, 113041.
[http://dx.doi.org/10.1016/j.jphotochem.2020.113041]
[25]
Mohamadpour, F. New role for photoexcited organic dye, Na2 eosin Y via the direct hydrogen atom transfer (HAT) process in photochemical visible-light-induced synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under air atmosphere. Dyes Pigments, 2021, 194, 109628.
[http://dx.doi.org/10.1016/j.dyepig.2021.109628]
[26]
Kidwai, M.; Chauhan, R. A rapid and an efficient route to the one-pot, multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione ring systems. J. Heterocycl. Chem., 2014, 51(6), 1689-1696.
[http://dx.doi.org/10.1002/jhet.1809]
[27]
Hosseininasab, N.; Davoodnia, A.; Rostami-Charati, F.; Khojastehnezhad, A. Preparation, characterization, and first catalytic application of a novel phosphotungstic acid-containing ionic liquid immobilized on CuFe2O4@SiO2 magnetic nanoparticles in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Russ. J. Gen. Chem., 2017, 87(10), 2436-2443.
[http://dx.doi.org/10.1134/S1070363217100267]
[28]
Shaikh, M.A.; Farooqui, M.; Abed, S. [Bu3NH][HSO4] catalyzed: an eco-efficient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Res. Chem. Intermed., 2018, 44(9), 5483-5500.
[http://dx.doi.org/10.1007/s11164-018-3435-8]
[29]
Azarifar, D.; Badalkhani, O.; Abbasi, Y.; Hasanabadi, M. Urea-functionalized silica-coated Fe3−x Ti x O4 magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. J. Indian Chem. Soc., 2017, 14(2), 403-418.
[http://dx.doi.org/10.1007/s13738-016-0989-5]
[30]
(a) Wang, W.; Cong-Hao, L.; Yi, Y.; Xiao-Jun, L.; Hong-Yun, G. An improved procedure for the three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using basic ionic liquid. J. Chem. Res., 2016, 40(6), 354-357.
[http://dx.doi.org/10.3184/174751916X14627996968714];
(b) Raghuvanshi, D.S.; Singh, K.N. A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies. Tetrahedron Lett., 2011, 52(43), 5702-5705.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.111]
[31]
Ziarani, G.M.; Mohtasham, N.H.; Badiei, A.; Lashgari, N. Efficient one-pot solvent-free synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones catalyzed by sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H). J. Chin. Chem. Soc. (Taipei), 2014, 61(9), 990-994.
[http://dx.doi.org/10.1002/jccs.201300538]
[32]
Reddy, M.V.; Kumar, P.C.R.; Reddy, G.C.S.; Reddy, C.S. Silica gel-supported tungstic acid (STA): A new, highly efficient and recyclable catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione carbonitriles and carboxylates under neat conditions. C. R. Chim., 2014, 17(12), 1250-1256.
[http://dx.doi.org/10.1016/j.crci.2014.01.026]
[33]
Piltan, M. Preparation of 1 H -pyrazolo[1,2- b]phthalazine-5,10-diones using ZrO 2 nanoparticles as a catalyst under solvent-free conditions. Heterocycl. Commun., 2017, 23(5), 401-403.
[http://dx.doi.org/10.1515/hc-2017-0142]
[34]
Lamera, E.; Bouacida, S.; Merazig, H.; Chibani, A.; Le Borgne, M.; Bouaziz, Z.; Bouraiou, A. DMAP as a new efficient catalyst for the one-pot synthesis of condensed phthalazines. Z. Natufoschr., 2017, 72(5), 361-368.
[http://dx.doi.org/10.1515/znb-2016-0262]
[35]
Tayade, Y.A.; Dalal, D.S. Cyclodextrin as a supramolecular catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives in water. Catal. Lett., 2017, 147(6), 1411-1421.
[http://dx.doi.org/10.1007/s10562-017-2032-6]
[36]
Tayebee, R.; Maleki, B. sabeti, M. A new simple method for the preparation of PbO nanoparticles and implementation of an efficient and reusable catalytic system for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. J. Indian Chem. Soc., 2017, 14(6), 1179-1188.
[http://dx.doi.org/10.1007/s13738-017-1068-2]
[37]
Kefayati, H.; Delafrooz, A.; Homayoon, S. Ultrasound-assisted synthesis of pyrazolo[1,2-b]phthalazines and dihydrospiro[indoline-3,1′-pyrazolo[1,2-b]phthalazines] using TBAF as an efficient phase-transfer catalyst. Russ. J. Gen. Chem., 2016, 86(7), 1735-1740.
[http://dx.doi.org/10.1134/S107036321607032X]
[38]
Khazaei, A.; Zolfigol, M.A.; Karimitabar, F.; Nikokar, I.; Moosavi-Zare, A.R.N. 2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media. RSC Advances, 2015, 5(87), 71402-71412.
[http://dx.doi.org/10.1039/C5RA10730J]
[39]
Ebrahimiasl, H.; Azarifar, D.; Mohammadi, M.; Keypour, H. Mahmood abadi, M. Synthesis of Fe3O4-supported Schiff base Cu (II) complex: a novel efficient and recyclable magnetic nanocatalyst for one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives. Res. Chem. Intermed., 2021, 47(2), 683-707.
[http://dx.doi.org/10.1007/s11164-020-04293-7]
[40]
Chalaki, S.B.; Akhlaghinia, B. CuII Anchored onto the magnetic talc: A new magnetic nanostructured catalyst for the one-pot gram-scale synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. ChemistrySelect, 2020, 5(35), 11010-11019.
[http://dx.doi.org/10.1002/slct.202002099]
[41]
Bashti, A.; Kiasat, A.R.; Mokhtari, B. Synthesis and characterization of dicationic 4,4′-bipyridinium dichloride ordered mesoporous silica nanocomposite and its application in the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. RSC Advances, 2015, 5(33), 25816-25823.
[http://dx.doi.org/10.1039/C4RA17067A]
[42]
Fallah-Ghasemi Gildeh, S.; Mehrdad, M.; Roohi, H.; Ghauri, K.; Fallah-Ghasemi Gildeh, S.; Rad-Moghadam, K. Experimental and DFT mechanistic insights into one-pot synthesis of 1 H -pyrazolo[1,2- b]phthalazine-5,10-diones under catalysis of DBU-based ionic liquids. New J. Chem., 2020, 44(38), 16594-16601.
[http://dx.doi.org/10.1039/D0NJ03478A]
[43]
Khaleghi, A.M.; Azarifar, D. Alanine-functionalized magnetic graphene oxide quantum dots: an efficient and recyclable heterogeneous basic catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and 2,3-dihydroquinazolin-4(1H)-one derivatives. Appl. Organomet. Chem., 2020, 2020, e5872.
[http://dx.doi.org/10.1002/aoc.5872]
[44]
Maleki, B.; Barat, S.; Sedigh, S. amaneh; Rezaee, S. E.; Moeinpour, F.; Khojastehnezhad, A.; Tayebee, R. Cesium carbonate supported on hydroxyapatite-encapsulated Ni0.5Zn0.5Fe2O4 nanocrystallites as a novel magnetically basic catalyst for the one-pot synthesis of pyrazolo[1,2-b]phthalazine-5,10-diones. Appl. Organomet. Chem., 2015, 29(5), 290-295.
[http://dx.doi.org/10.1002/aoc.3288]
[45]
Maheswari, C.S.; Tamilselvi, V.; Ramesh, R.; Lalitha, A. An organocatalytic cascade synthesis of diverse 1H-pyrazolo[1,2-b]phthalazine-2-carboxamide, 1H-Pyrazolo[1,2- b]phthalazine, 4H-Pyrano[2,3-c]pyrazole and 4H benzo[g]chromenes via multicomponent reactions. Org. Prep. Proc. Int., 2020, 52(1), 22-36.
[http://dx.doi.org/10.1080/00304948.2019.1693241]
[46]
Maleki, B.; Nejat, R.; Alinezhad, H.; Mousavi, S.M.; Mahdavi, B.; Delavari, M. Nanostructural Cu-Doped ZnO hollow spheres as an economical and recyclable catalyst in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and pyrazolo[1,2-a][1,2,4]triazole-1,3-diones. Org. Prep. Proc. Int., 2020, 52(4), 328-339.
[http://dx.doi.org/10.1080/00304948.2020.1765655]
[47]
Shafe-Mehrabadi, S.R.; Sadeghi, B.; Hassanabadi, A. SiO2-H2SO4 Nanoparticles: A solid phase acidic catalyst and an efficient for one-pot synthesis of 3,9-diamino-5,10-dioxo-1-aryl-5,10-dihydropyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives. Polycycl. Aromat. Compd., 2022, 42(2), 574-581.
[http://dx.doi.org/10.1080/10406638.2020.1747094]
[48]
Saadati-Moshtaghin, H.R.; Zonoz, F.M. Synthesis and characterization of magnetically recoverable 1-(copperferritesiloxypropyl)-3-methylimidazolium heteropolytungstate ionic liquid as a new nanocatalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. J. Nanostructure Chem., 2017, 7(4), 317-325.
[http://dx.doi.org/10.1007/s40097-017-0241-6]
[49]
Hamidinasab, M.; Bodaghifard, M.A.; Mobinikhaledi, A. Green synthesis of 1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives using a new bifunctional baseionic liquid hybrid magnetic nanocatalys. Appl. Organomet. Chem., 2019, 2019, e5386.
[http://dx.doi.org/10.1002/aoc.5386]
[50]
Sangani, C.B.; Makwana, J.A.; Duan, Y.T.; Thumar, N.J.; Zhao, M.Y.; Patel, Y.S.; Zhu, H.L. Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity. Res. Chem. Intermed., 2016, 42(3), 2101-2117.
[http://dx.doi.org/10.1007/s11164-015-2138-7]
[51]
Wang, J.; Bai, X.; Xu, C.; Wang, Y.; Lin, W.; Zou, Y.; Shi, D. Ultrasound-promoted one-pot, three-component synthesis of spiro[indoline-3,1′-pyrazolo[1,2-b]phthalazine] derivatives. Molecules, 2012, 17(7), 8674-8686.
[http://dx.doi.org/10.3390/molecules17078674] [PMID: 22825620]
[52]
Zhang, X.N.; Li, Y.X.; Zhang, Z.H. Nickel chloride-catalyzed one-pot three-component synthesis of pyrazolophthalazinyl spirooxindoles. Tetrahedron, 2011, 67(38), 7426-7430.
[http://dx.doi.org/10.1016/j.tet.2011.07.002]
[53]
Jadhav, A.M.; Balwe, S.G.; Kim, J.S.; Lim, K.T.; Jeong, Y.T. Indium(III)chloride catalyzed synthesis of novel 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under solvent-free condition. Tetrahedron Lett., 2019, 60(7), 560-565.
[http://dx.doi.org/10.1016/j.tetlet.2019.01.028]
[54]
Shi, X.; Ding, M.; Li, C.; Wang, W.; Guo, H. A green synthesis of highly functionalized 3-amino-2-phenylsulfonyl-1-alkyl/aryl-1H-pyrazolo[1,2-b]phthalazine-5,10-diones and their reduction and photophysical studies. J. Heterocycl. Chem., 2018, 55(2), 440-446.
[http://dx.doi.org/10.1002/jhet.3061]
[55]
Sabitha, G.; Srinivas, C.; Raghavendar, A.; Yadav, J.S. Phosphomolybdic acid (PMA)-SiO2 as a heterogeneous solid acid catalyst for the one-pot synthesis of 2H-Indazolo[1,2-b]phthalazine-triones. Helv. Chim. Acta, 2010, 93(7), 1375-1380.
[http://dx.doi.org/10.1002/hlca.200900378]
[56]
Kiasat, A.R.; Davarpanah, J. Fe3O4@silica sulfuric acid nanoparticles: An efficient reusable nanomagnetic catalyst as potent solid acid for one-pot solvent-free synthesis of indazolo[2,1-b]phthalazine-triones and pyrazolo[1,2-b]phthalazine-diones. J. Mol. Catal. Chem., 2013, 373, 46-54.
[http://dx.doi.org/10.1016/j.molcata.2013.03.003]
[57]
Sagar Vijay Kumar, P.; Suresh, L.; Chandramouli, G.V.P. Ionic liquid catalysed multicomponent synthesis, antifungal activity, docking studies and in silico ADMET properties of novel fused Chromeno-Pyrazolo-Phthalazine derivatives. J. Saudi Chem. Soc., 2017, 21(3), 306-314.
[http://dx.doi.org/10.1016/j.jscs.2015.08.001]
[58]
Dabiri, M. Combining a click-multicomponent reaction: One-pot synthesis of (1,2,3-triazol-4-yl)methyl 3-amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate derivatives. Synth. Commun., 2014, 44(14), 2037-2044.
[http://dx.doi.org/10.1080/00397911.2014.888080]
[59]
(a) Teimouri, M.B. One-pot three-component reaction of isocyanides, dialkyl acetylenedicarboxylates and phthalhydrazide: synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Tetrahedron, 2006, 62(47), 10849-10853.
[http://dx.doi.org/10.1016/j.tet.2006.09.006];
(b) Ansari, M.D.; Sagir, H.; Yadav, V.B. Magnetically recoverable Fe3O4 nanocatalyst for the synthesis of biodynamically significant 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives and its DFT study. Mol. Divers., 2022.
[http://dx.doi.org/10.1007/s11030-022-10532-3]
[60]
Hasthavaram, S.; Reddy, N.A.; Kamala, K.; Dayam, R.; Saritha, K.V. One-pot synthesis of phthalazinyl-2-carbonitrile indole derivatives via [BMIM][OH] as ionic liquid and their anticancer evaluation and molecular modeling studies. Eur. Chem. Bull., 2020, 9(7), 154-159.
[http://dx.doi.org/10.17628/ecb.2020.9.154-159]
[61]
Rao, R.K.; Kankala, S. One-pot green synthesis of 3-amino-1-(5-nitro-1H-indol-2-yl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile. Eur. Chem. Bull., 2019, 7(11-12), 324-328.
[http://dx.doi.org/10.17628/ecb.2018.7.324-328]
[62]
Sagar, S.S.; Chavan, R.P. SiO2:MgMnO3: an efficient heterogeneous catalyst for one pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Asian J. Chem., 2020, 32(10), 2489-2494.
[http://dx.doi.org/10.14233/ajchem.2020.22707]
[63]
Roy, H.N.; Rana, M.; Munsur, A.Z.A.; Lee, K.I.; Sarker, A.K. Efficient and convenient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline. Synth. Commun., 2016, 46(16), 1370-1376.
[http://dx.doi.org/10.1080/00397911.2016.1192650]
[64]
Banerjee, D.; Maiti, G. An efficient one-pot four-component synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives catalyzed by proline. Indian J. Chem. Sect. B, 2019, 58B(6), 674-679.
[65]
Mohamadpour, F.; Maghsoodlou, M.T.; Heydari, R.; Lashkari, M. Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions. Res. Chem. Intermed., 2016, 42(12), 7841-7853.
[http://dx.doi.org/10.1007/s11164-016-2565-0]
[66]
Kerru, N.; Gummidi, L.; Bhaskaruni, S.V.H.S.; Maddila, S.N.; Jonnalagadda, S.B. One-pot green synthesis of novel 5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine derivatives with eco-friendly biodegradable eggshell powder as efficacious catalyst. Res. Chem. Intermed., 2020, 46(6), 3067-3083.
[http://dx.doi.org/10.1007/s11164-020-04135-6]
[67]
Mohamadpour, F. Carboxymethyl cellulose (CMC) as a recyclable green catalyst promoted eco-friendly protocol for the solvent-free synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Polycycl. Aromat. Compd., 2022, 42(4), 1091-1102.
[http://dx.doi.org/10.1080/10406638.2020.1768412]
[68]
Shaterian, H.R.; Mohammadnia, M. Mild preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under ambient and solvent-free conditions. Res. Chem. Intermed., 2014, 40(1), 371-383.
[http://dx.doi.org/10.1007/s11164-012-0969-z]
[69]
Shaterian, H.R.; Mohammadnia, M. Mild basic ionic liquids catalyzed new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. J. Mol. Liq., 2012, 173, 55-61.
[http://dx.doi.org/10.1016/j.molliq.2012.06.007]
[70]
Jeevan Raghavendra, G.; Siddaiah, V. One-pot four component synthesis of 3-amino-1-(1H-indol-2-yl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]pht-halazine derivatives mediated by [DBUH] [OAc]. Russ. J. Gen. Chem., 2018, 88(9), 1892-1898.
[http://dx.doi.org/10.1134/S1070363218090219]
[71]
Safaei-Ghomi, J.; Shahbazi-Alavi, H.; Ziarati, A.; Teymuri, R.; Saberi, M.R. A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with CuI nanoparticles as catalyst under solvent-free conditions. Chin. Chem. Lett., 2014, 25(3), 401-405.
[http://dx.doi.org/10.1016/j.cclet.2013.11.046]
[72]
Zaky, O.S.; Selim, M.A.; Ebied, M.M.; Sadek, K.U. Glycerol: A promising benign solvent for catalyst‐free one‐pot multi‐component synthesis of 1H‐Pyrozolo[1,2‐b]phthalazine‐5,10‐diones and 2H‐Indazolo[2,1‐b]phthalazine‐triones under controlled microwaves irradiation. J. Heterocycl. Chem., 2019, 56(10), 2796-2803.
[http://dx.doi.org/10.1002/jhet.3659]
[73]
Pouramiri, B.; Far, R.G.; Zahedifar, M. Acidic ionic liquids: highly efficient catalysts for one-pot four-component synthesis of pyrazolo[1,2-b]phthalazines under solvent-free conditions. Chem. Heterocycl. Compd., 2018, 54(11), 1056-1060.
[http://dx.doi.org/10.1007/s10593-018-2391-y]
[74]
Amirmahani, N.; Mahmoodi, N.O.; Malakootian, M.; Pardakhty, A. Introducing new and effective catalysts for the synthesis of pyridazino[1,2-a]indazole, indazolo[2,1-b]phthalazine and pyrazolo[1,2-b]phthalazine derivatives. MethodsX, 2020, 7, 100823.
[http://dx.doi.org/10.1016/j.mex.2020.100823] [PMID: 32195140]
[75]
Mohamadpour, F. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): as a highly efficient bicyclic amidine catalyst promoted solvent-free and one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Indian J. Chem. Sect. B, 2020, 59B(8), 1234-1242.
[76]
Mohamadpour, F. Theophylline as a green catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Org. Prep. Proc. Int., 2020, 52(1), 64-68.
[http://dx.doi.org/10.1080/00304948.2019.1697611]
[77]
Mohamadpour, F. Caffeine: a green, natural and biodegradable catalyst for convenient and expedient eco-safe synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives under solvent-free conditions. Indian J. Chem. Sect. B, 2019, 58B(12), 1398-1406.
[78]
Mohamadpour, F.; Maghsoodlou, M.T.; Heydari, R.; Lashkari, M. Saccharin: a green, economical and efficient catalyst for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole. J. Indian Chem. Soc., 2016, 13(8), 1549-1560.
[http://dx.doi.org/10.1007/s13738-016-0871-5]
[79]
Song, S.H.; Zhong, J.; He, Y.H.; Guan, Z. One-pot four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Tetrahedron Lett., 2012, 53(52), 7075-7077.
[http://dx.doi.org/10.1016/j.tetlet.2012.10.063]
[80]
Soheilizad, M.; Adib, M.; Sajjadifar, S. One-pot and solvent-free synthesis of aliphatic and aromatic 1H-indazolo[2,1-b]phthalazinetriones catalyzed by boron sulfonic acid. Monatsh. Chem., 2014, 145(8), 1353-1356.
[http://dx.doi.org/10.1007/s00706-014-1194-9]
[81]
Tavakoli, H.R.; Moosavi, S.M.; Bazgir, A. ZrOCl2.8H2O as an efficient catalyst for the three-component synthesis of triazoloindazoles and indazolophthalazines. J. Korean Chem. Soc., 2013, 57(4), 472-475.
[http://dx.doi.org/10.5012/jkcs.2013.57.4.472]
[82]
Jia, X.C.; Li, J.; Ding, Y.; Wang, N.; Wang, Y.H. A simple and green protocol for 2H-Indazolo[2,1-b]phthalazine-triones using grinding method. J. Chem., 2013, 2013, 634510.
[http://dx.doi.org/10.1155/2013/634510]
[83]
Varghese, A.; Nizam, A.; Kulkarni, R.; George, L. Solvent-free synthesis of 2H-indazolo[2,1-b] phthalazine-triones promoted by cavitational phenomenon using iodine as catalyst. Eur. J. Chem., 2013, 4(2), 132-137.
[http://dx.doi.org/10.5155/eurjchem.4.2.132-137.746]
[84]
Shaterian, H.R.; Fahimi, N.; Azizi, K. New applications of phosphoric acid supported on alumina (H3PO4-Al2O3) as a reusable heterogeneous catalyst for preparation of 2,3-dihydroquinazoline-4(1H)-ones, 2H-indazolo[2,1-b]phthalazinetriones, and benzo[4,5]imidazo[1,2-a]pyrimidines. Res. Chem. Intermed., 2014, 40(5), 1879-1898.
[http://dx.doi.org/10.1007/s11164-013-1087-2]
[85]
Kiasat, A.R.; Noorizadeh, S.; Ghahremani, M.; Saghanejad, S.J. Experimental and theoretical study on one-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones catalyzed by nano-alumina sulforic acid. J. Mol. Struct., 2013, 1036, 216-225.
[http://dx.doi.org/10.1016/j.molstruc.2012.11.014]
[86]
Mulik, A.; Chandam, D.; Patil, P.; Patil, D.; Jagdale, S.; Deshmukh, M. Proficient synthesis of quinoxaline and phthalazinetrione derivatives using [C8dabco]Br ionic liquid as catalyst in aqueous media. J. Mol. Liq., 2013, 179, 104-109.
[http://dx.doi.org/10.1016/j.molliq.2012.12.006]
[87]
Shirini, F.; Langarudi, M.S.N.; Goli-Jolodar, O. Synthesis of 2 H- indazolo[2,1- b]phthalazine-1,6,11(13 H)-triones using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate DABCO(HSO3)2 (HSO4)2 as a new ionic liquid catalyst. Dyes Pigments, 2015, 123, 186-195.
[http://dx.doi.org/10.1016/j.dyepig.2015.07.036]
[88]
Goli-Jolodar, O.; Shirini, F.; Seddighi, M. Introduction of a novel nanosized N-sulfonated Bronsted acidic homogeneous catalyst for the promotion of the synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones. J. Nanosci. Nanotechnol., 2018, 18(1), 591-603.
[http://dx.doi.org/10.1166/jnn.2018.13922] [PMID: 29768885]
[89]
Iravani, N.; Keshavarz, M.; Parhami, A. Novel SO3H-functionalized phenanthrolinum-phosphotungstate ionic liquid for highly promoted three-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones. Res. Chem. Intermed., 2019, 45(10), 5045-5066.
[http://dx.doi.org/10.1007/s11164-019-03875-4]
[90]
Goli-Jolodar, O.; Shirini, F. Catalysis of indazolophthalazinetriones by ionic liquid - succinimidinium hydrogen sulfate. Theor. Exp. Chem., 2017, 52(6), 349-357.
[http://dx.doi.org/10.1007/s11237-017-9489-7]
[91]
Zare, A.; Masihpour, F. Novel ionic liquid N,N -diethyl- N -sulfoethanaminium hydrogen sulfate: Design, characterization, and application as a highly efficient catalyst for the production of triazolo[1,2- a]indazole-triones and 2 H -indazolo[2,1- b]phthalazine-triones. Phosphorus Sulfur Silicon Relat. Elem., 2016, 191(8), 1160-1165.
[http://dx.doi.org/10.1080/10426507.2016.1149853]
[92]
Tayebee, R.; Jomei, M.; Maleki, B.; Razi, M.K.; Veisi, H.; Bakherad, M. A new natural based ionic liquid 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones. J. Mol. Liq., 2015, 206, 119-128.
[http://dx.doi.org/10.1016/j.molliq.2015.02.021]
[93]
Yang, F.; Zang, H.J.; Wang, Q.K.; Cheng, B.W.; Ren, Y.L.; Xu, X.L. One-pot Syntheses of 2H-indazolo[2,1-b] phthalazine-triones catalyzed by ionic Iiquid. Adv. Mat. Res., 2011, 332-334, 1884-1887.
[http://dx.doi.org/10.4028/www.scientific.net/AMR.332-334.1884]
[94]
Mombani Godajdar, B.; Reza Kiasat, A.; Mahmoodi Hashemi, M. One-pot synthesis of 2H-indazolo[2,1-b]phthalazinetrione catalyzed by magnetic room temperature dicationic ionic liquid under solvent-free conditions. Heterocycles, 2013, 87(3), 559-570.
[http://dx.doi.org/10.3987/COM-12-12626]
[95]
Mousapour, M.; Shirini, F.; Abedini, M. Efficient synthesis of 2H-indazolo[2,1-b]phthalazine-triones using [PVPH]ClO4 as a modified polymeric catalyst. Polycycl. Aromat. Compd., 2021, 41(2), 419-426.
[http://dx.doi.org/10.1080/10406638.2019.1593863]
[96]
Veeranarayana Reddy, M.; Reddy, G.C.S.; Jeong, Y.T. Microwave-assisted, montmorillonite K-10 catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Tetrahedron, 2012, 68(34), 6820-6828.
[http://dx.doi.org/10.1016/j.tet.2012.06.045]
[97]
Mazaahir, K.; Ritika, C.; Anwar, J. Efficient CAN catalyzed synthesis of 1H-indazolo[1,2-b] phthalazine-1,6,11-triones: An eco-friendly protocol. Chin. Sci. Bull., 2012, 57(18), 2273-2279.
[http://dx.doi.org/10.1007/s11434-012-5081-7]
[98]
Shi, X.; Li, J.; Zhong, W.; Li, J. Synthesis of 1 H -indazolo[2,1-b]phthalazine-triones catalysed by proline triflate under solvent-free conditions. J. Chem. Res., 2012, 36(1), 17-20.
[http://dx.doi.org/10.3184/174751912X13251821462738]
[99]
Kidwai, M.; Jahan, A.; Chauhan, R.; Mishra, N.K. Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Tetrahedron Lett., 2012, 53(14), 1728-1731.
[http://dx.doi.org/10.1016/j.tetlet.2012.01.095]
[100]
Wang, X.; Ma, W.W.; Wu, L.Q.; Yan, F.L. Synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives using wet cyanuric chloride under solvent-free condition. J. Chin. Chem. Soc. (Taipei), 2010, 57(6), 1341-1345.
[http://dx.doi.org/10.1002/jccs.201000198]
[101]
Kiasat, R.; Mouradezadegun, A.; Saghanezhad, J. Phospho sulfonic acid: A novel and efficient solid acid catalyst for the one-pot preparation of 2H-indazolo[2,1-b]-phthalazine-triones. J. Serb. Chem. Soc., 2013, 78(4), 469-476.
[http://dx.doi.org/10.2298/JSC120508088K]
[102]
Turhan, K.; Turgut, Z. Efficient one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-trione derivatives catalyzed by Y(OTf)3. Russ. J. Org. Chem., 2019, 55(2), 250-253.
[http://dx.doi.org/10.1134/S1070428019020180]
[103]
Maleki, B.; Ashrafi, S.S.; Tayebee, R. One-Pot Synthesis of 2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione derivatives using nano hybrid MoO3/α-Al2O3. Org. Prep. Proc. Int., 2017, 49(6), 542-548.
[http://dx.doi.org/10.1080/00304948.2017.1384260]
[104]
Choudhury, A.; Ali, S.; Khan, A.T. Khan, T. Hydrated ferric sulfate [Fe2(SO4)3·xH2O]: an efficient and reusable catalyst for one-pot synthesis of 2H-indazole[2,1-b]phthalazine-triones. J. Korean Chem. Soc., 2015, 59(4), 280-283.
[http://dx.doi.org/10.5012/jkcs.2015.59.4.280]
[105]
Salehi, P. MaGee, D.I.; Dabiri, M.; Torkian, L.; Donahue, J. Combining click-multicomponent reaction: one-pot synthesis of triazolyl methoxy-phenyl indazolo[2,1-b]phthalazine-trione derivatives. Mol. Divers., 2012, 16(2), 231-240.
[http://dx.doi.org/10.1007/s11030-011-9348-8] [PMID: 22161122]
[106]
Pavithra, D.; Ethiraj, K.R. Tetrabutylammonium bromide (TBAB) promoted metal-free synthesis of 2H-indazolo[1,2-b]phthalazinetriones and pyrazolo[1,2-b]phthalazines from benzylalcohol through aerobic oxidation, sequential addition-cyclization with phthalhydrazide and β-diketones. Polycycl. Aromat. Compd., 2022, 42(2), 344-357.
[http://dx.doi.org/10.1080/10406638.2020.1732430]
[107]
Amarasekara, A.S.; Chandrasekara, S. Reaction of 1,4-phthalazinedione with furfural: formation of the [5,6]benza-3a,7a-diazaindane system via an unusual skeletal rearrangement. Org. Lett., 2002, 4(5), 773-775.
[http://dx.doi.org/10.1021/ol017256+] [PMID: 11869124]
[108]
Heine, H.W.; Henrie, R.; Heitz, L.; Kovvali, S.R. Diaziridines. III. Reactions of some 1-alkyl- and 1,1-dialkyl-1H-diazirino[1,2b]phthalazine-3,8-diones. J. Org. Chem., 1974, 39(22), 3187-3191.
[http://dx.doi.org/10.1021/jo00936a001]

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