Abstract
Reactions of diazomethane with quinone mono(di)imines and methylidene quinone imines of pyrido[1,2-a]benzimidazole series occurs by the route of 1,3-dipolar cycloaddition and leads to the formation of quinoid compounds, in particular, previously unknown heterocyclic structures of indazolo[7',6':4,5]imidazo-[2,1-j]quinoline, indazolo[7',6':4,5]imidazo[2,1-e]acridine, indazolo[4',5':4,5]imidazo[2,1-j]quinoline, and indazolo[4',5':4,5]imidazo[2,1-e]acridine.
Similar content being viewed by others
References
Ulrich, H., Richter, R. Methoden der Organische Chemie, Houben, I. and Weil, T., Eds., Stuttgart Thieme Verlag, 1977.
Eistert, B., Fink, H., and Müller, A., Chem. Ber., 1962, vol. 95, p. 2403. doi 10.1002/cber.19620951012
Da Silva, E.N.Jr., de Souza, M.C.B.V., Fernandes, M.C., Menna-Barreto, R.F.S., Pinto, M.C.F.R., de Assis Lopes, F., de Simone, C.A., Andrade, C.K.Z., Pinto, A.V., Ferreira, V.F., and de Castro, S.L., Bioorg. Med. Chem., 2008, vol. 16, p. 5030. doi 10.1016/j.bmc.2008.03.032
Carneiro, P.F., Do Nascimento, S.B., Pinto, A.V., Pinto, M.C.F.R., Lechuga, G.C., Santos, D.O., Dos Santos Júnior, H.M., Resende, J.A.L.C., Bourguignon, S.C., and Ferreira, V.F., Bioorg. Med. Chem., 2012, vol. 20, p. 4995. doi 10.1016/j.bmc.2012.06.027
The Chemistry of the Quinonoid Compounds, Patai, S., and Rappoport, Z., Eds., Chichester: Wiley, 1988, vol. 2.
Dean, F.M., Houghton, L.T., Nayyir-Mashir, R., and Thebtaranonth, C., J. Chem. Soc., Perkin Trans. 1, 1980, p. 1994. doi 10.1039/P19800001994
Takeya, T., Kajiyama, M., Nakamura, C., and Tobinaga, S., Chem. Pharm. Bull., 1999, vol. 47, p. 209. doi 10.1248/cpb.47.209
Komissarova, N.L., Belostotskaya, I.S., Vol’eva, V.B., Dzhuaryan, E.V., Novikova, I.A., and Ershov, V.V., Russ. Chem. Bull., 1981, vol. 30, p. 1944. doi 10.1007/BF00963430
Laatsch, H., Renneberg, B., Duvernay, E., and Schmidt, A.J., Z. Naturforsch. B, 1995, vol. 50, p. 151.
Eistert, B., Pfleger, K., Arackal, T.J., and Holzer, G., Chem. Ber., 1975, vol. 108, p. 693. doi 10.1002/cber.19751080235
Ott, R. and Pinter, E., Monatsh. Chem., 1992, vol. 123, p. 713. doi 10.1007/BF00812321
Hassan, M.A., Fandy, R.F., and El-Amine, T.M., J. Heterocycl. Chem., 2001, vol. 38, p. 179. doi 10.1002/jhet.5570380126
Tapia, R.A., Carrasco, C., Ojeda, S., Salas, C., Valderrama, J.A., Morello, A., and Repetto, Y., J. Heterocycl. Chem., 2002, vol. 39, p. 1093. doi 10.1002/jhet.5570390540
Tandon, V.K., Yadav, D.B., Chaturvedi, A.K., and Shukla, P.K., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 3288. doi 10.1016/j.bmcl.2005.04.066
Bader, A.R. and Ettlinger, M.G., J. Am. Chem. Soc., 1953, vol. 75, p. 730. doi 10.1021/ja01099a066
Agarwal, N.L., Bohnstengel, H., and Schaefer, W., J. Heterocycl. Chem., 1984, vol. 21, p. 825. doi 10.1002/jhet.5570210337
Laatsch, H., Lieb. Ann., 1985, p. 251. doi 10.1002/jlac.198519850205
Farina, F., Peredes, M.C., and Stefani, V., Tetrahedron, 1986, vol. 42, p. 4309. doi 10.1016/S0040-4020(01)87657-2
Legentil, L., Benel, L., Bertrand, V., Lesur, B., and Delfourne, E., J. Med. Chem., 2006, vol. 49, p. 2979. doi 10.1021/jm051247f
Adams, R. and Reifschneider, W., Bull. Soc. Chim., 1958, vol. 23, p. 23.
Jones, G.W., Kerur, D.R., Yamazaki, T., Shecter, H., Woolhouse, A.D., and Halton, B., J. Org. Chem., 1974, vol. 39, p. 492.
Pinkus, A.G. and Tsuji, J., J. Org. Chem., 1974, vol. 39, p. 497.
Bespalov, B.P. and Titov, V.V., Russ. Chem. Rev., 1975, vol. 44, p. 1091. doi 10.1070/RC1975v044n12ABEH002559
Slabko, O.Yu., Britsina, O.I., and Kaminskii, V.A., Chem. Heterocycl. Compd., 1991, vol. 27, p. 788. doi 10.1007/BF00476215
Slabko, O.Yu., Shandova, O.N., and Kaminskii, V.A., Russ. J. Org. Chem., 2009, vol. 45, p. 425. doi 10.1134/S1070428009030130
Slabko, O.Yu., Verbitskii, G.A., and Kaminskii, V.A., Chem. Heterocycl. Compd., 2006, vol. 42, p. 358. doi 10.1007/s10593-006-0093-3
Slabko, O.Yu., Borzova, O.V., and Kaminskii, V.A., Russ. J. Org. Chem., 2014, vol. 50, p. 1133. doi 10.1134/S1070428014080107
Fizer, L. and Fizer, M., Reagenty dlya organicheskogo sinteza (Reagents for Organic Synthesis), Moscow: Mir, 1970, vol. 1.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © O.Yu. Slabko, N.V. Ageenko, V.A. Denisenko, V.A. Kaminskii, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 237–241.
Rights and permissions
About this article
Cite this article
Slabko, O.Y., Ageenko, N.V., Denisenko, V.A. et al. 1,3-dipolar cycloaddition of diazomethane to quinoid derivatives of pyrido[1,2-a]benzimidazole. Russ J Org Chem 53, 231–235 (2017). https://doi.org/10.1134/S1070428017020154
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428017020154