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ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

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General Review Article

Diverse Routes for the Synthesis of Indole-Fused Complex Architecture from Simple Molecules

Author(s): Shivendra Singh, Suresh Singh Chauhan, Neeraj Kumar Sharma, Sunil Dutt and Keshav Lalit Ameta*

Volume 18, Issue 2, 2021

Published on: 21 May, 2020

Page: [237 - 258] Pages: 22

DOI: 10.2174/1570193X17999200521101255

Price: $65

Abstract

Several easy, efficient and convenient procedures to access indoles fused heterocyclic systems are described in this review. These heterocyclic systems were synthesized from several cyclic or acyclic molecules via a variety of reactions such as Diels-Alder reaction, Michael addition, Morita- Baylis-Hillmann reaction and many other domino/Cascade approaches with high selectivity. Most of the given protocols in this review proceed through organocatalytic pathways; however, some underwent different catalytic and non-catalytic reactions.

Keywords: Analgesic, domino approach, indole heterocycles, multicomponent reactions, nootropic agents, organocatalysis, psychoanaleptic.

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Graphical Abstract

[1]
Takada, S.; Ishizuka, N.; Sasatani, T.; Makisumi, Y.; Jyoyama, H.; Hatakeyama, H.; Asanuma, F.; Hirose, K. Studies on fused indoles. II. Structural modifications and analgesic activity of 4-amino-methyltetrahydrothiopyrano[2,3-b]indoles. Chem. Pharm. Bull. (Tokyo), 1984, 32(3), 877-886.
[http://dx.doi.org/10.1248/cpb.32.877] [PMID: 6744491]
[2]
Makisumi, Y.; Sasatani, T. Tetrahydrothiopyrano[3,2-b]indole derivatives. U.S. Patent No. 4910318,. 1990.
[3]
Ishizuka, N.; Sato, T.; Makisumi, Y. Indole Grignard reaction. III. Synthesis, crystal structure, and analgesic activity of (R)- and (S)-3-amino-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoles. Chem. Pharm. Bull. (Tokyo), 1990, 38(5), 1396-1399.
[http://dx.doi.org/10.1248/cpb.38.1396] [PMID: 2393965]
[4]
Pereira, N.A.L.; Sureda, F.X.; Pérez, M.; Amat, M.; Santos, M.M.M. Enantiopure indolo[2,3-a]quinolizidines: Synthesis and evaluation as NMDA receptor antagonists. Molecules, 2016, 21(8)E1027
[http://dx.doi.org/10.3390/molecules21081027]] [PMID: 27509489]
[5]
Jia, W.B.; Wang, H.W.; Yang, L.M.; Lu, H.B.; Kong, L.; Tian, Y.P.; Tao, X.; Yang, J.X. Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property. J. Mater. Chem. C Mater. Opt. Electron. Devices, 2013, 42, 7092-7101.
[http://dx.doi.org/10.1039/c3tc31590h]
[6]
Zhang, Z-Z.; Liu, B.; Wang, C.Y.; Shi, B-F. Cobalt(III)-catalyzed C2-selective C-H alkynylation of indoles. Org. Lett., 2015, 17(16), 4094-4097.
[http://dx.doi.org/10.1021/acs.orglett.5b02038] [PMID: 26263117]
[7]
Xie, X.; Du, X.; Chen, Y.; Liu, Y. One-pot synthesis of indole-fused scaffolds via gold-catalyzed tandem annulation reactions of 1,2-bis(alkynyl)-2-en-1-ones with indoles. J. Org. Chem., 2011, 76(21), 9175-9181.
[http://dx.doi.org/10.1021/jo2017668] [PMID: 21939236]
[8]
Yao, B.; Wang, Q.; Zhu, J. Palladium(II)-catalyzed intramolecular diamination of alkynes under aerobic oxidative conditions: Catalytic turnover of an iodide ion. Angew. Chem. Int. Ed. Engl., 2012, 51(21), 5170-5174.
[http://dx.doi.org/10.1002/anie.201201640] [PMID: 22499532]
[9]
Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D.W. A flexible, palladium-catalyzed indole and azaindole synthesis by direct annulation of chloroanilines and chloroaminopyridines with ketones. Angew. Chem. Int. Ed. Engl., 2004, 43(34), 4526-4528.
[http://dx.doi.org/10.1002/anie.200460122] [PMID: 15340961]
[10]
Samala, S.; Arigela, R.K.; Kant, R.; Kundu, B. Diversity-oriented synthesis of ketoindoloquinoxalines and indolotriazoloquinoxalines from 1-(2-nitroaryl)-2-alkynylindoles. J. Org. Chem., 2014, 79(6), 2491-2500.
[http://dx.doi.org/10.1021/jo402783p] [PMID: 24571484]
[11]
Gupta, S.; Koley, D.; Ravikumar, K.; Kundu, B. Counter ion effect in Au/Ag-catalyzed chemoselective 6-endo-dig N- and O-cyclizations of enyne-urea system: Diversity-oriented synthesis of annulated indoles. J. Org. Chem., 2013, 78(17), 8624-8633.
[http://dx.doi.org/10.1021/jo4013332] [PMID: 23899005]
[12]
Dighe, S.U.; Mahar, R.; Shukla, S.K.; Kant, R.; Srivastava, K.; Batra, S. Synthesis of S-(-)-5,6-dihydrocanthin-4-ones via a triple cooperative catalysis-mediated domino reaction. J. Org. Chem., 2016, 81(11), 4751-4761.
[http://dx.doi.org/10.1021/acs.joc.6b00613] [PMID: 27159615]
[13]
Arigela, R.K.; Mandadapu, A.K.; Sharma, S.K.; Kumar, B.; Kundu, B. Cascade intermolecular Michael addition-intramolecular azide/internal alkyne 1,3-dipolar cycloaddition reaction in one pot. Org. Lett., 2012, 14(7), 1804-1807.
[http://dx.doi.org/10.1021/ol300399y] [PMID: 22440058]
[14]
Holloway, C.A.; Muratore, M.E.; Storer, R.L.; Dixon, D.J. Direct enantioselective Brønsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids. Org. Lett., 2010, 12(21), 4720-4723.
[http://dx.doi.org/10.1021/ol101651t] [PMID: 20929214]
[15]
Purohit, P.; Pandey, A.K.; Kumar, B.; Chauhan, P.M.S. Diversity oriented synthesis of β-carbolinone and indolo-pyrazinone analogues based on an Ugi four component reaction and subsequent cyclisation of the resulting indole intermediate. RSC Advances, 2016, 6, 21165-21186.
[http://dx.doi.org/10.1039/C5RA27090A]
[16]
Thikekar, T.U.; Selvaraju, M.; Sun, C.M. Skeletally diverse synthesis of indole-fused diazocine and diazepine frameworks by one-pot, two-component cascade reaction. Org. Lett., 2016, 18(2), 316-319.
[http://dx.doi.org/10.1021/acs.orglett.5b03481] [PMID: 26735127]
[17]
Jaiswal, P.K.; Biswas, S.; Singh, S.; Samanta, S. An organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water. Org. Biomol. Chem., 2013, 11(48), 8410-8418.
[http://dx.doi.org/10.1039/c3ob42034e] [PMID: 24189837]
[18]
Jaiswal, P.K.; Biswas, S.; Singh, S.; Pathak, B.; Mobin, S.M.; Samanta, S. Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael-Henry reaction: An easy access to four contiguous chiral centers. RSC Advances, 2013, 3, 10644-10649.
[http://dx.doi.org/10.1039/c3ra41409d]
[19]
Biswas, S.; Jaiswal, P.K.; Singh, S.; Mobin, S.M.; Samanta, S. L-proline catalyzed stereoselective synthesis of (E)-methyl-α-indol-2-yl-β-aryl/alkyl acrylates: Easy access to substituted carbazoles, γ-carbolines and prenostodione. Org. Biomol. Chem., 2013, 11(41), 7084-7087.
[http://dx.doi.org/10.1039/c3ob41573b] [PMID: 24057205]
[20]
Chen, X.Y.; Wen, M.W.; Ye, S.; Wang, Z.X. Unusual formal [4 + 2] cycloaddition of ethyl allenoate with arylidenoxindoles: Synthesis of dihydropyran-fused indoles. Org. Lett., 2011, 13(5), 1138-1141.
[http://dx.doi.org/10.1021/ol103165y] [PMID: 21302968]
[21]
Ali, S.; Li, Y.X.; Anwar, S.; Yang, F.; Chen, Z.S.; Liang, Y.M. One-pot access to indolo[2,3-b]quinolines by electrophile-triggered cross-amination/Friedel-Crafts alkylation of indoles with 1-(2-tosylaminophenyl)ketones. J. Org. Chem., 2012, 77(1), 424-431.
[http://dx.doi.org/10.1021/jo202035p] [PMID: 22136250]
[22]
Karkhelikar, M.V.; Rao, V.V.; Shinde, S.S.; Likhar, P.R. A new synthetic approach to pyrrolo[3,2-b]indoles via regioselective formation of pyrrole and intramolecular C-N coupling. Tetrahedron Lett., 2016, 57, 4803-4806.
[http://dx.doi.org/10.1016/j.tetlet.2016.09.044]
[23]
Majumdar, K.C.; Taher, A.; Ray, K. Domino-Knoevenagel-Hetero-Diels-Alder reactions: An efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives. Tetrahedron Lett., 2009, 50, 3889-3891.
[http://dx.doi.org/10.1016/j.tetlet.2009.04.054]
[24]
Jiang, M.; Li, J.; Wang, F.; Zhao, Y.; Zhao, F.; Dong, X.; Zhao, W. A facile copper-catalyzed one-pot domino synthesis of 5,12-dihydroindolo[2,1-b]quinazolines. Org. Lett., 2012, 14(6), 1420-1423.
[http://dx.doi.org/10.1021/ol3001624] [PMID: 22394154]
[25]
Hu, J.D.; Cao, C.P.; Lin, W.; Hu, M.H.; Huang, Z.B.; Shi, D.Q. Selective synthesis of polyfunctionalized pyrido[2,3-b]indoles by multicomponent domino reactions. J. Org. Chem., 2014, 79(17), 7935-7944.
[http://dx.doi.org/10.1021/jo501049m] [PMID: 25078565]
[26]
Xu, S.; Zhou, Y.; Xu, J.; Jiang, H.; Liu, H. Gold-catalyzed Michael addition/intramolecular annulation cascade: An effective pathway for the chemoselective- and regioselective synthesis of tetracyclic indole derivatives in water. Green Chem., 2013, 15, 718-726.
[http://dx.doi.org/10.1039/c2gc36301a]
[27]
Moghaddam, F.M.; Ghanbari, B.; Behzadi, M.; Baghersad, M.H. Synthesis of tetrahydrothiopyrano[2,3-b]indole [60]fullerene derivatives via Hetero-Diels-Alder reaction of C60 and α,β-unsaturated indole-2-thiones. J. Heterocycl. Chem., 2017, 54, 911-915.
[http://dx.doi.org/10.1002/jhet.2653]
[28]
Arigela, R.K.; Sharma, S.K.; Kumar, B.; Kundu, B. Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles. Beilstein J. Org. Chem., 2013, 9, 401-405.
[http://dx.doi.org/10.3762/bjoc.9.41] [PMID: 23504610]
[29]
Ohta, Y.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. Concise synthesis of indole-fused 1,4-diazepines through copper(I)-catalyzed domino three-component coupling-cyclization-N-arylation under microwave irradiation. Org. Lett., 2008, 10(16), 3535-3538.
[http://dx.doi.org/10.1021/ol801383b] [PMID: 18616342]
[30]
Yang, L.; Wang, F.; Chua, P.J.; Lv, Y.; Zhong, L.J.; Zhong, G. N-Heterocyclic Carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles. Org. Lett., 2012, 14(11), 2894-2897.
[http://dx.doi.org/10.1021/ol301175z] [PMID: 22594458]
[31]
Dagar, A.; Biswas, S.; Samanta, S. A catalyst-free, efficient green MCR protocol for access to functionalized γ-carbolines in water. RSC Advances, 2015, 5, 52497-52507.
[http://dx.doi.org/10.1039/C5RA08422A]
[32]
Yu, J.; Zhang-Negrerie, D.; Du, Y. Cu(OAc)2-Mediated cascade annulation of diarylalkyne sulfonamides through dual C-N bond formation: Synthesis of 5,10-dihydroindolo[3,2-b]indoles. Org. Lett., 2016, 18(14), 3322-3325.
[http://dx.doi.org/10.1021/acs.orglett.6b01343] [PMID: 27366912]
[33]
Yu, S.; Li, Y.; Zhou, X.; Wang, H.; Kong, L.; Li, X. Access to structurally diverse quinoline-fused heterocycles via Rhodium(III)-catalyzed C-C/C-N coupling of bifunctional substrates. Org. Lett., 2016, 18(12), 2812-2815.
[http://dx.doi.org/10.1021/acs.orglett.6b01032] [PMID: 27267178]
[34]
Chen, X.; Zhang, J.Q.; Yin, S.J.; Li, H.Y.; Zhou, W.Q.; Wang, X.W. Asymmetric construction of spiro[thiopyranoindole-benzoisothiazole] scaffold via a formal [3+3] spiroannulation. Org. Lett., 2015, 17(17), 4188-4191.
[http://dx.doi.org/10.1021/acs.orglett.5b01951] [PMID: 26287438]
[35]
Srivastava, A.; Biswas, S.; Singh, S.; Mobin, S.M.; Samanta, S. Organocatalysed Michael addition on arylmethylidene malonates involving 4-(2-nitrophenyl)acetoacetate: Diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds. RSC Advances, 2015, 5, 26891-26896.
[http://dx.doi.org/10.1039/C5RA01430A]
[36]
Abbiati, G.; Canevari, V.; Caimi, S.; Rossi, E. Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles: A new entry to [1,4]oxazino[4,3-a]indoles. Tetrahedron Lett., 2005, 46, 7117-7120.
[http://dx.doi.org/10.1016/j.tetlet.2005.08.102]
[37]
Takada, S.; Makisumi, Y. Studies on fused Indole I. Novel synthesis of 4-aminomethyltetrahydrothiopyrano[2,3-b]indole through a Thio-Claisen rearrangement. Chem. Pharm. Bull. (Tokyo), 1984, 32, 872-876.
[http://dx.doi.org/10.1248/cpb.32.872]
[38]
Majumdar, K.C.; Debnath, P.; Alam, S.; Maji, P.K. Thiol-mediated radical cyclization: Regioselective formation of indole-annulated sulfur heterocycles by tandem cyclization. Tetrahedron Lett., 2007, 48, 7031-7033.
[http://dx.doi.org/10.1016/j.tetlet.2007.07.132]
[39]
Moghaddam, F.M.; Kiamehr, M.; Taheri, S.; Mirjafary, Z. Synthesis of novel polycyclic indole-annulated thiopyranocoumarin derivatives via domino Knoevenagel-hetero-Diels-Alder reaction in aqueous media. Helv. Chim. Acta, 2010, 93, 964-973.
[http://dx.doi.org/10.1002/hlca.200900324]
[40]
Majumder, S.; Bhuyan, P.J. Synthesis of some novel and complex thiopyranoindole derivatives from simple oxindole via intramolecular domino hetero Diels-Alder reactions. Tetrahedron Lett., 2012, 53, 137-140.
[http://dx.doi.org/10.1016/j.tetlet.2011.10.133]
[41]
Majumder, S.; Bhuyan, P.J. Stereoselective synthesis of novel annulated thiopyranoindole derivatives from simple oxindole via intramolecular 1,3-dipolar cycloaddition reactions of nitrone and nitrile oxide. Tetrahedron Lett., 2012, 53, 762-764.
[http://dx.doi.org/10.1016/j.tetlet.2011.11.136]
[42]
Moghaddam, F.M.; Mirjafary, Z.; Saeidian, H.; Kiamehr, M.; Taheri, S.; Kiamehr, M. Facile entry to polycyclic indolylhydroquinoline skeletons via tandem C-alkylation and intramolecular S-alkylation. Tetrahedron, 2010, 66, 134-138.
[http://dx.doi.org/10.1016/j.tet.2009.11.032]
[43]
Moghaddam, F.M.; Foroushani, B.K.; Sobhani, M.; Masoud, N.; Khodabakhshi, M.R.; Weng, N.S. The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylise-Hillman adduct acetates. Tetrahedron, 2013, 69, 8169-8173.
[http://dx.doi.org/10.1016/j.tet.2013.07.043]
[44]
Jha, M.; Edmunds, M.; Lund, K.; Ryan, A. A new route to the versatile synthesis of thiopyrano[2,3-b:6,5-b′]diindoles via 2-(alkylthio)-indole-3-carbaldehydes. Tetrahedron Lett., 2014, 55, 5691-5694.
[http://dx.doi.org/10.1016/j.tetlet.2014.08.100]
[45]
Wu, L.; Wang, Y.; Zhou, Z. Stereocontrolled construction of the dihydrothiopyrano[2,3-b]indole skeleton via an organocatalyzed asymmetric cascade sulfa-Michael-Aldol reaction. Tetrahedron Asymmetry, 2014, 25, 1389-1395.
[http://dx.doi.org/10.1016/j.tetasy.2014.09.005]
[46]
Chen, X.; Qi, Z.H.; Zhang, S.Y.; Kong, L.P.; Wang, Y.; Wang, X.W. Enantioselective construction of functionalized thiopyrano-indole annulated heterocycles via a formal thio [3 + 3]-cyclization. Org. Lett., 2015, 17(1), 42-45.
[http://dx.doi.org/10.1021/ol503210q] [PMID: 25517293]
[47]
Jha, M.; Shelke, G.M.; Cameron, T.S.; Kumar, A. Access to substituted dihydrothiopyrano[2,3-b]indoles via sequential rearrangements during S-alkylation and Au-catalyzed hydroarylation on indoline-2-thiones. J. Org. Chem., 2015, 80(10), 5272-5278.
[http://dx.doi.org/10.1021/jo5025943] [PMID: 25894662]
[48]
Shelke, G.M.; Jha, M.; Kumar, A. Synthesis of indole-annulated sulfur heterocycles using copper-catalysed C-N coupling and palladium-catalysed direct arylation. Org. Biomol. Chem., 2016, 14(13), 3450-3458.
[http://dx.doi.org/10.1039/C6OB00117C] [PMID: 26964635]
[49]
Singh, S.; Srivastava, A.; Samanta, S. Rapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives via one-pot three component reaction using organocatalysis. Tetrahedron Lett., 2012, 53, 6087-6090.
[http://dx.doi.org/10.1016/j.tetlet.2012.08.125]
[50]
Murugesh, V.; Bruneau, C.; Achard, M.; Sahoo, A.R.; Sharma, G.V.M.; Suresh, S. Ruthenium catalyzed β-C(sp3)-H functionalization on the ‘privileged’ piperazine nucleus. Chem. Commun. (Camb.), 2017, 53(75), 10448-10451.
[http://dx.doi.org/10.1039/C7CC05604D] [PMID: 28884776]
[51]
Chen, K.; Tang, X.Y.; Shi, M. Rh(II)-Catalyzed formation of pyrrolo[2,3-b]quinolines from azide-methylenecyclopropanes and isonitriles. Chem. Commun. (Camb.), 2016, 52(9), 1967-1970.
[http://dx.doi.org/10.1039/C5CC09236A] [PMID: 26686901]
[52]
Dhole, S.; Chiu, W.J.; Sun, C.M. Catalyst-controlled chemodivergent annulation to indolo/pyrrolo-fused diazepine and quinoxaline. Adv. Synth. Catal., 2019, 361, 2916-2925.
[http://dx.doi.org/10.1002/adsc.201900088]

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