Abstract
Cascade cyclization of methyl 2-(azidomethyl)furan-3-carboxylate with 2-cyanoacetamides in the presence of 2 equiv of potassium tert-butoxide afforded a series of N-substituted 5-oxo-5,9-dihydro-4H-furo-[3,2-e][1,2,3]triazolo[1,5-a][1,3]diazepine-3-carboxamides.
References
Barluenga, J., Tomas, M., Ballesteros, A., Kong, J.-S., Granda, S.G., and Perez-Carreno, E., J. Chem. Soc., Chem. Commun., 1991, p. 353.
Barluenga, J., Tomas, M., Ballesteros, A., and Kong, J.-S., Synthesis, 1992, p. 106.
Zimmer, H., Nauss, J.L., and Amer, A., J. Heterocycl. Chem., 1998, vol. 35, p. 25.
Zimmer, H., Amer, A., Ho, D., and Palmer-Sungail, R., J. Heterocycl. Chem., 1991, vol. 28, p. 1501.
Zimmer, H., Librera, C.P., Hausner, S., Bauer, J., and Amer, A., Molecules, 2003, vol. 8, p. 735.
Funke, C., Es-Sayed, M., and de Meijere, A., Org. Lett., 2000, vol. 2, p. 4249.
Tsuchiga, T., Enkaku, M., and Okajima, S., J. Chem. Soc., Chem. Commun., 1980, p. 454.
Ozer, M.S., Koza, G., Sahin, E., and Balci, M., Tetrahedron Lett., 2013, vol. 54, p. 6553.
Eres’ko, O.B., Tolkunov, V.S., Suikov, S.Yu., and Tolkunov, S.V., Dopov. Nats. Akad. Nauk Ukr., 2011, no. 3, p. 143.
Povazanec, F., Decroix, B., and Morel, J., J. Heterocycl. Chem., 1992, vol. 29, p. 1507.
Feng, X., Lancelot, J.-C., Prumier, H., and Rault, S., J. Heterocycl. Chem., 1996, vol. 33, p. 2007.
Viti, G., Giannotti, D., Nannicini, R., Ricci, R., and Pestellini, V., J. Heterocycl. Chem., 1990, vol. 27, p. 1369.
Ivashtchenko, A.V., Golovina, E.S., Kadieva, M.G., Koryakova, A.G., Kovalenko, S.M., Mitkin, O.O., Okun, J.M., Ravnyayko, J.M., Tkachenko, S.E., and Zaremba, O.V., J. Comb. Chem., 2010, vol. 12, p. 445.
Pokhodylo, N.T. and Matiychuk, V.S., J. Heterocycl. Chem., 2010, vol. 47, p. 415.
Lee, K., Campbell, J., Swoboda, J.G., Cuny, G.D., and Walker, S., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 1767.
Bratenko, M.K., Barus, M.M., and Vovk, M.V., Chem. Heterocycl. Compd., 2015, vol. 50, p. 1707.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © M.S. Yagodkina, G.G. Yakovenko, A.V. Bol’but, M.V. Vovk, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 626–627.
Rights and permissions
About this article
Cite this article
Yagodkina, M.S., Yakovenko, G.G., Bol’but, A.V. et al. Cascade cyclization of methyl 2-(azidomethyl)furan-3-carboxylates with 2-cyanoacetamides. Efficient synthesis of a new heterocyclic system, furo[3,2-e][1,2,3]triazolo- [1,5-a][1,3]diazepine. Russ J Org Chem 53, 634–636 (2017). https://doi.org/10.1134/S1070428017040261
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428017040261