Abstract
The reaction of butyrolactone acetal with CH acids was used to synthesize 2-methylenetetrahydrofuran derivatives. The latter react with dimethylformimide acetal to give a dieneamine that is capable of undergoing cyclization to furo [3,2-c]pyrimidine derivatives. This two-ring system was also synthesized by the reaction of cyanacetamide with 3-dimethylaminomethylenebutyrolactone acetal. The indicated acetal can also react with amidine components to give furo [2,3-d]pyrimidine derivatives.
Similar content being viewed by others
Literature cited
J. Gloede, L. Haase, and H. Gross, Z. Chem., 9, 201 (1969).
V. G. Granik, A. M. Zhidkova, and R. G. Glushkov, Usp. Khim., 46, 685 (1977).
H. Meerwein, P. Borner, O. Fuchs, H. J. Sasse, H. Schrode, and J. Spille, Chem. Ber., 89, 2060 (1956).
N. B. Marchenko, V. G. Granik, I. V. Persianova, and R. G. Glushkov, Khim. Geterotsikl, Soedin., No. 6, 737 (1980).
A. M. Zhidkova, V. G. Granik, N. S. Kuryatov, V. P. Pakhomov, O. S. Anisimova, and R. G. Glushkov, Khim. Geterotsikl. Soedin., No. 8, 1089 (1974).
V. G. Granik, M. K. Polievktov, and R. G. Glushkov, Zh. Org. Khim., 7, 1431 (1971).
V. G. Granik, O. Ya. Belyaeva, R. G. Glushkov, T. F. Vlasova, A. B. Grigor'ev, and M. K. Polievktov, Khim. Geterotsikl. Soedin., No. 11, 1518 (1977).
H. Brederek, J. Simchen, and B. Funke, Chem. Ber., 104, 2709 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 68–71, January, 1982.
Rights and permissions
About this article
Cite this article
Marchenko, N.B., Granik, V.G. Synthesis of furo[3,2-c]pyridine and furo[2,3-d]pyrimidine derivatives from butyrolactone diethylacetal. Chem Heterocycl Compd 18, 58–61 (1982). https://doi.org/10.1007/BF00513290
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00513290