Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

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

HIGHLIGHTS

The Synthesis of New Selenium-containing Heterocycles by the Oxidation Reaction of 2,4-Diaryltetrahydro-4H-selenochromenes

Author(s): Dmitriy Yurievich Direnko*, Boris Ivanovich Drevko and Yaroslav Borisovich Drevko

Volume 24, Issue 15, 2020

Page: [1663 - 1668] Pages: 6

DOI: 10.2174/1385272824999200720165656

Price: $65

Abstract

We have explored the reactions of tetrahydro-4H-selenochromenes in the presence of phosphoric pentachloride, and synthesized new condensate aroylbenzoselenophenes. During the reactions, tetrahydro-4H-selenochromenes with phosphoric pentachloride underwent oxidative aromatization and nucleophilic substitution for a chlorine atom of one of the protons in the alicyclic fragment. Also, the narrowing of the heterocyclic fragment occurred as in synthesized selenium-containing compounds earlier transformed into the corresponding condensate aroylbenzoselenophenes.

Keywords: Synthesis, heterocycles, 2, 4-diaryltetrahydro-4H-selenochromenes, aroylbenzoselenophenes, 1, 5-diketones, pummerer rearrangement.

Next »
Graphical Abstract
[1]
Jun, F.W.; Mei, Z.; Long, Z.L. Synthesis of 3,3-disubstituted oxindoles by organoselenium-induced radical cyclizations of N-arylacrylamides. Heterocycl. Commun., 2015, 21, 9-12.
[http://dx.doi.org/10.1515/hc-2014-0195]
[2]
Al-Tamimi, A.S.; Mitxeltorena, M.E.; Sanmartín, C.; Ruiz, A.J.; Syrjänen, L.; Parkkila, S.; Selleri, S.; Carta, F.; Angeli, A.; Supuran, C.T. Discovery of new organoselenium compounds as antileishmanial agents. Bioorg. Chem., 2019, 86, 339-345.
[http://dx.doi.org/10.1016/j.bioorg.2019.01.069] [PMID: 30743174]
[3]
Spengler, G.; Gajdács, M.; Marć, M.A.; Álvarez, E.D.; Sanmartín, C. Organoselenium compounds as novel adjuvants of chemotherapy drugs-A promising approach to fight cancer drug resistance. Molecules, 2019, 24(2), 336.
[http://dx.doi.org/10.3390/molecules24020336] [PMID: 30669343]
[4]
Guan, Q.; Yang, F.; Guo, D.; Xu, J.; Jiang, M.; Liu, C.; Bao, K.; Wu, Y.; Zhang, W. Synthesis and biological evaluation of novel 3,4-diaryl-1,2,5-selenadiazol analogues of combretastatin A-4. Eur. J. Med. Chem., 2014, 87, 1-9.
[http://dx.doi.org/10.1016/j.ejmech.2014.09.046] [PMID: 25233100]
[5]
Wang, L.; Fu, J.N.; Wang, J.Y.; Jin, C.J.; Ren, X.Y.; Tan, Q.; Li, J.; Yin, H.W.; Xiong, K.; Wang, T.Y.; Liu, X.M.; Zeng, H.H. Selenium-containing thioredoxin reductase inhibitor ethaselen sensitizes non-small cell lung cancer to radiotherapy. Anticancer Drugs, 2011, 22(8), 732-740.
[http://dx.doi.org/10.1097/CAD.0b013e32834618bc] [PMID: 21562407]
[6]
Balkrishna, S.J.; Bhakuni, B.S.; Chopra, D.; Kumar, S. Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles. Org. Lett., 2010, 12(23), 5394-5397.
[http://dx.doi.org/10.1021/ol102027j] [PMID: 21053969]
[7]
Abdel-Hafez, S.H. Selenium containing heterocycles: synthesis, anti-inflammatory, analgesic and antimicrobial activities of some new 4-cyanopyridazine-3(2H)selenone derivatives. Eur. J. Med. Chem., 2008, 43(9), 1971-1977.
[http://dx.doi.org/10.1016/j.ejmech.2007.12.006] [PMID: 18242782]
[8]
Potapov, V.A.; Musalov, M.V.; Kurkutov, E.O. Synthesis of new functionalized organoselenium compounds by heterocyclization of selenium dihalides with pent-4-en-1-ol. J. Org. Chem., 2016, 50, 360-363.
[http://dx.doi.org/10.1134/S1070428016030088]
[9]
Santi, C.; Santoro, S.; Battistelli, B. Organoselenium compounds as catalysts in nature and laboratory. Curr. Org. Chem., 2010, 14(20), 2442-2462.
[http://dx.doi.org/10.2174/138527210793358231]
[10]
Varlamova, E.G.; Goltyaev, M.V.; Kuznetsova, J.P. Effect of sodium selenite on gene expression of self, selw, and TGR selenoproteins in adenocarcinoma cells of the human prostate. Mol. Biol. (Mosk.), 2018, 52(3), 519-526.
[http://dx.doi.org/10.7868/S0026898418030151] [PMID: 29989584]
[11]
Spallholz, J.E. Selenomethionine and methioninase: selenium free radical anticancer activity. Methods Mol. Biol., 2019, 1866, 199-210.
[http://dx.doi.org/10.1007/978-1-4939-8796-2_15] [PMID: 30725417]
[12]
Drevko, B.I.; Borodulin, V.B.; Rusetskaja, N.J.; Drevko, J.B.; Borodulin, J.V.; Babushkina, I.V.; Raguzina, V.I.; Ivanov, A.B. 2,6-Diphenyl-4-("n"- metoxyphenyl)-4-selenopyran - medication for treatment and prevention of poison-ing with mercury compounds. R.U. Patent 2455987C1, July 20, 2012.
[13]
Hassan, W.; Oliveira, C.S.; Noreen, H.; Kamdem, J.P.; Nogueira, C.W.; Rocha, J.B.T. Organoselenium compounds as potential neuroprotective therapeutic agents. Curr. Org. Chem., 2016, 20(2), 218-231.
[http://dx.doi.org/10.2174/1385272819666150810222632]
[14]
Khurana, A.; Tekula, S.; Saifi, M.A.; Venkatesh, P.; Godugu, C. Therapeutic applications of selenium nanoparticles. Biomed. Pharmacother., 2019, 111, 802-812.
[http://dx.doi.org/10.1016/j.biopha.2018.12.146] [PMID: 30616079]
[15]
Ha, H.Y.; Alfulaij, N.; Berry, M.J.; Seale, L.A. From selenium absorption to selenoprotein degradation. Biol. Trace Elem. Res., 2019, 192(1), 26-37.
[http://dx.doi.org/10.1007/s12011-019-01771-x] [PMID: 31222623]
[16]
Ying, H.; Zhang, Y. Systems biology of selenium and complex disease. Biol. Trace Elem. Res., 2019, 192(1), 38-50.
[http://dx.doi.org/10.1007/s12011-019-01781-9] [PMID: 31236815]
[17]
Reddy, D.B.; Reddy, A.S.; Padmavathi, V.; Babu, N.C. Synthesis of 5,7-diphenyl (-4-alkyl)trihydropyrano|3,4-d||1,2,3| selenadiazoles and 5,7-diphenyl(-1-alkyl)trihydropyrano|3,4-d||1,2,3|thiadiazoles. Heterocycl. Commun., 2000, 6, 271-274.
[http://dx.doi.org/10.1515/HC.2000.6.3.271]
[18]
Javahershenas, R.; Khalafy, J. A new synthesis of pyrrolo[3,2-d]pyrimidine derivates by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst. Heterocycl. Commun., 2018, 24, 37-41.
[http://dx.doi.org/10.1515/hc-2017-0187]
[19]
Sabegh, M.A.; Khalafy, J. The regioselective catalyst-free synthesis of bis-quinoxalines and bis-pyrido[2,3-b]pyrazines by double condensation of 1,4-phenylene-bis-glyoxal with 1,2-diamines. Heterocycl. Commun., 2018, 24, 193-196.
[http://dx.doi.org/10.1515/hc-2018-0039]
[20]
Barcellos, A.M.; Abenante, L.; Sarro, M.T.; Leo, I.D.; Lenardao, E.J.; Perin, G.; Santi, C. New prospective for redox modulation mediated by organo selenium and organotellurium compounds. Curr. Org. Chem., 2017, 21(20), 2044-2061.
[http://dx.doi.org/10.2174/1385272820666161020162113]
[21]
Wieczorek, E.; Piskorz, J.; Popenda, L.; Jurga, S.; Mielcarek, J.; Goslinski, T. Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmet-hyl) amino groups - synthesis and optical properties. Heterocycl. Commun., 2019, 25, 1-7.
[http://dx.doi.org/10.1515/hc-2019-0001]
[22]
Wu, D.; Liu, M.; Li, Z.; Dang, M.; Liu, X.; Li, J.; Huang, L.; Ren, Y.; Zhang, Z.; Liu, W.; Liu, A. Synthesis and fungicidal activity of novel imidazo[4,5-b]pyridine derivatives. Heterocycl. Commun., 2019, 25, 8-14.
[http://dx.doi.org/10.1515/hc-2019-0003]
[23]
Zaki, R.M.; El-Dean, A.M.K.; Radwan, S.M.; Saber, A.F. Efficient synthesis, reactions and spectral characterization of pyrazolo[4′,3′:4,5]thieno[3,2-d]pyrimidines and related heterocycles. Heterocycl. Commun., 2019, 25, 39-46.
[http://dx.doi.org/10.1515/hc-2019-0004]
[24]
Sonawane, A.D.; Koketsu, M. Recent advances on C-Se bond-forming reactions at low and room temperature. Curr. Org. Chem., 2019, 23(28), 3206-3225.
[http://dx.doi.org/10.2174/1385272823666191209111934]
[25]
Zhang, Y.; Shao, Y.; Gong, J.; Zhu, J.; Cheng, T.; Chen, J. Selenium-catalyzed oxidative C-H amination of (E)-3-(Arylamino)-2-styrylquinazolin-4(3H)-ones: a metal-free synthesis of 1,2-diarylpyrazolo[5,1- b]quinazolin-9(1H)-ones. J. Org. Chem., 2019, 84(5), 2798-2807.
[http://dx.doi.org/10.1021/acs.joc.8b03179] [PMID: 30740976]
[26]
Direnko, D.Y.; Drevko, Y.B.; Drevko, B.I. The synthesis of new organoselenium heterocyclic compounds: 2-aryl-4-phenyl-5,6,7,8-tetrahydro-4H-sele-nochromenes. J. Chin. Chem. Soc. (Taipei), 2015, 62, 1068-1071.
[http://dx.doi.org/10.1002/jccs.201500406]
[27]
Drevko, B.I.; Fomenko, L.A.; Smuhskin, M.I.; Zhukov, O.I.; Kharchenko, V.G. Synthesis of 5,6-polymethyleneselenopyryllium salts. Chem. Heterocycl. Commun., 1994, 30(6), 503-504.
[http://dx.doi.org/10.1007/BF01169954]
[28]
Kharchenko, V.G.; Drevko, B.I. Reactions of 1,5-dicetones with hydrogen selenide in the presence of trifluoroacetic acid. Chem. Heterocycl. Commun., 1985, 21(12), 1345-1348.
[http://dx.doi.org/10.1007/BF00505956]
[29]
Drevko, B.I.; Bol’shakova, E.G.; Almaeva, A.F.; Suchkov, M.A.; Mandych, V.G.; Shekhter, G.A. A novel reaction of 2,4,6-triphenyl(thio)selenopyry-lium salts leading to benzoyl(thio)selenophenes and 2,4,6-triphenyl(thio)sele-nopyrans. Russ. Chem. Bull. Int. Ed., 2009, 58, 1526-1527.
[http://dx.doi.org/10.1007/s11172-009-0207-z]
[30]
Direnko, D.Yu.; Drevko, B.I.; Drevko, Ya.B. Synthesis of first selenodecalines: 2-aryl-4-phenyloctahydroselenochromenes. Heterocycl. Commun., 2016, 22, 227-228.
[http://dx.doi.org/10.1515/hc-2016-0076]
[31]
Drevko, B.I.; Zhukov, O.I.; Kharchenko, V.G. Reactions of 1,5-diaryl-pentandion-1, 5-pentanediones and 1,5-diaryl-3-(thia)selenapentandion-1,5 with PCl5. Russ. J. Org. Chem., 1995, 31, 1548-1552.
[32]
Barton, D.; Ollis, W.D. Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds; Pergamon Press, 1979.
[33]
Lambert, J.B.; Featherman, S.I. Conformational analysis of pentamethylen heterocycles. Chem. Rev., 1975, 75, 611-626.
[http://dx.doi.org/10.1021/cr60297a005]
[34]
Lambert, J.B.; Mixan, C.E.; Johnson, D.H. Axial preferensin selenanes. Tetrahedron Lett., 1972, 43, 4335-4338.
[35]
Drevko, B.I.; Suchkova, E.V.; Baranchikova, G.A.; Mandych, Y.G. New thermal rearrangement of 2,4,6-triarylthio(seleno)pyrylium salts. Russ. Chem. Bull. Int. Ed., 2006, 55(10), 1867-1868.
[36]
Kharchenko, V.G.; Chalaya, S.N. Thiopyrans and Thiapyrilium’s Salts; Publishing House of Saratov State University: Saratov, 1987, p. 60.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy