Abstract
Condensation of o-cyanomethylbenzoic acids with esters of 2-aminothiophene-3-carboxylic and 3-amino-thiophene-2-carboxylic acids to give isomeric 2-(4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylmethyl)-benzoic acids and their ethyl and phenacyl esters. Methylation of esters occurs at N-3. The spectroscopic characteristics of the positional isomers are compared at the level of carboxylic acids, their esters, and methylated products.
Similar content being viewed by others
References
V. A. Kovtunenko, T. T. Kucherenko, O. V. Shishkin, and V. M. Kisel. Khim. Geterotsikl. Soed., 1408 (2002). [Chem. Heterocycl. Comp., 38, 1242 (2002)].
V. A. Kovtunenko, T. T. Kucherenko, R. I. Zubatyuk, O. V. Shishkin, and D. A. Yushchenko. Khim. Geterotsikl. Soed., 1532 (2007). [Chem. Heterocycl. Comp., 43, 1301 (2007)].
W. Reid and R. Giesse. Liebigs Ann. Chem., 713, 143 (1968).
M. Perrissin, M. Favre, C. L. Duc, F. Huguet, C. Gaulthier, and G. Narcisse. Eur. J. Med. Chem. Chim. Ther., 23, 453 (1988).
V. A. Kovtunenko, Z. V. Voitenko, V. L. Sheptun, A. K. Tyltin, A. I. Chernega, Yu. T. Struchkov, and F. S. Babichev. Khim. Geterotsikl. Soed., 1497 (1984). [Chem. Heterocycl. Comp., 20, 1235 (1984)].
J. S. Aggarwal, R. S. Das, and J. N. N. Ray. J. Indian Chem. Soc., 6, 717 (1929). Chem. Abstr., 24, 1113 (1930).
D. J. Brown, E. Hoerger, and S. F. Mason. J. Chem. Soc., 211 (1955).
H. Culbertson, J. C. Decius, and B. E. Christensen. J. Amer. Chem. Soc., 74, 4834 (1952).
L. Bellamy. New Data on the Infrared Spectra of Complex Molecules [Russian translation]. Mir, Moscow (1971), p.175.
C. C. Price and R. G. Rogers in Synthesis of Organic Preparations [Russian translation]. Izd-vo inostr. lit., Moscow (1952), Vol. 3, 267.
Farbwerke Hoechst. Akt. Ges, Brit. Pat. 837 086 (1960); Chem. Abstr., 54, 24798 (1960).
K. Gewald, E. Schinke, and H. Böttcher, Chem. Ber., 99, 94 (1966).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 932–941, June, 2008.
Rights and permissions
About this article
Cite this article
Kucherenko, T.T., Zadorozhny, A.V. & Kovtunenko, V.A. Positional isomers of thienopyrimidinones. Chem Heterocycl Comp 44, 750–758 (2008). https://doi.org/10.1007/s10593-008-0100-y
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0100-y