Transformations of 3,3,4-tricyano-3,4-dihydro-2 H -pyran-4-carboxamides. Synthesis of pyrano[3,4- c ]pyrrole derivatives

M. Yu. Ievlev; O. V. Ershov; A. N. Vasil’ev; V. A. Tafeenko; M. D. Surazhskaya; O. E. Nasakin

doi:10.1134/S1070428017070119

Transformations of 3,3,4-tricyano-3,4-dihydro-2H-pyran-4-carboxamides. Synthesis of pyrano[3,4-c]pyrrole derivatives

Authors: Ievlev M.Y.¹, Ershov O.V.¹, Vasil’ev A.N.¹, Tafeenko V.A.², Surazhskaya M.D.³, Nasakin O.E.¹
Affiliations:
1. I.N. Ul’yanov Chuvash State University
2. Faculty of Chemistry
3. Kurnakov Institute of General and Inorganic Chemistry
Issue: Vol 53, No 7 (2017)
Pages: 1030-1035
Section: Article
URL: https://journals.rcsi.science/1070-4280/article/view/216537
DOI: https://doi.org/10.1134/S1070428017070119
ID: 216537

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Abstract

A procedure has been developed for the synthesis of polyfunctional pyrano[3,4-c]pyrrole derivatives via intramolecular cyclization involving vicinal cyano and carboxamide groups on a pyran ring. 3-Amino-1-oxo-1,3a,4,7a-tetrahydropyrano[3,4-c]pyrrole-3a,7a-dicarbonitrile thus obtained react with organic amines to give stable ammonium salts and undergo hydrolysis to 1,3-dioxo-1,2,3,3a,4,7a-hexahydropyrano[3,4-c]pyrrole-3a,7a-dicarbonitriles in the presence of sulfuric acid.