Abstract
The nitration of 1,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4-diones under different conditions led to the formation of their 6(7)-mono- and 6,7-dinitro derivatives which were reduced to the corresponding amines. The latter reacted with α- and β-dicarbonyl compounds, as well as with ortho-quinones to give a number of new polycyclic heteroaromatic systems.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Corey, E.J., Czakó, B., and Kürti, L., Molecules and Medicine, Hoboken, NJ: Wiley, 2007.
Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry, and Applications, Chichester: Wiley, 2011, 2nd ed.
Gribble, G.W., Indole Ring Synthesis: From Natural Products to Drug Discovery, Chichester: Wiley, 2016.
Tsupak, E.B., Tkachenko, Yu.N., and Pozharskii, A.F., Chem. Heterocycl. Compd., 1994, vol. 28, p. 1077.
Doddi, G., Mencarelli, P., Razzini, A., and Stegel, F., J. Org. Chem., 1979, vol. 44, p. 2321.
Grehn, L., Chem. Scripta, 1978, vol. 13, p.67.
Jones, R.A. and Bean, G.P., The Chemistry of Pyrroles, New York: Academic, 1977, p.124.
CAChe 4.4 for Windows, USA: CAChe Group, Fujitsu Systems Business of America. http: www.cachesoftware.com
Senga, K., Ichiba, M., and Nishigaki, S., J. Org. Chem., 1979, vol. 44, p. 3830.
SMART and SAINT, Release 5.0. Area Detector Control and Integration Software, Madison (USA; Bruker AXS, Analytical X-Ray Instruments, 1998.
Sheldrick, G.M., SADABS: A Program for Exploiting the Redundancy of Area Detector X-Ray Data, Göttingen (Germany), 1999.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p.112.
Spek, A.L., J. Appl. Crystallogr., 2003, vol. 36, p.7.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision D.01, Wallingford CT: Gaussian, 2003.
Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, p. 11623.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © Yu.N. Tkachenko, L.D. Popov, A.F. Pozharskii, S.A. Borodkin, S.I. Levchenkov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 10, pp. 1536–1543.
Rights and permissions
About this article
Cite this article
Tkachenko, Y.N., Popov, L.D., Pozharskii, A.F. et al. Nitro derivatives of pyrrolo[3,2-d]pyrimidine-2,4-diones: Synthesis of amines and new polynuclear heterocycles based thereon. Russ J Org Chem 53, 1564–1572 (2017). https://doi.org/10.1134/S1070428017100128
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428017100128