Abstract
Unlike rheumycin and fervenulin, isofervenulin and 3-methylisofervenulin are hydrolyzed by aqueous alkalies at the N(5)-C(6) bond. On acidification of the reaction mixture, the N-carboxy-N-methylcarbamoyltriazines formed are reconverted into the starting isofervenulins, and on basification (pH>10) into methylaminotriazinecarboxamides. A by-product of the alkaline hydrolysis of isofervenulin is a product of the contraction of the uracil ring, namely imidazotriazinone-7a-carboxylic acid.
Similar content being viewed by others
Literature Cited
A. I. Chernyshev, S. V. Shorshnev, N. I. Yakushkina, and S. E. Esipov, Khim. Geterotsikl. Soedin., No. 2, 277 (1985).
S. V. Shorshnev, S. E. Esipov, N. I. Yakushkina, N. A. Klyuev, V. G. Zhil'nikov, and A. I. Chernyshev, Khim. Geterotsikl. Soedin., No. 9, 1252 (1987).
L. Heinisch, J. Prakt. Chem., 311, 438 (1969).
A. F. Pozharskii, I. M. Navanyan, and V. V. Kuz'menko, Khim. Geterotsikl. Soedin., No. 11, 1564 (1983).
T. Tokuhiro and G. Fraenkel, J. Am. Chem. Soc., 91, 5005 (1969).
E. M. Karpitschka, G. Smole, and W. Klotzer, Sci. Pharm., 49, 453 (1981).
E. C. Taylor and F. Sowinsky, J. Am. Chem. Soc., 90, 1374 (1968).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1555–1559, November, 1987.
Rights and permissions
About this article
Cite this article
Shorshnev, S.V., Esipov, S.E., Chernyshev, A.I. et al. Different modes of alkaline hydrolysis of fervenulin and isofervenulin. Chem Heterocycl Compd 23, 1247–1251 (1987). https://doi.org/10.1007/BF00479380
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00479380