SYNTHESIS OF SUBSTITUTED 4-AMINOTHIENO[2,3-<i>d</i>]-, 4-AMINOTHIENO[3,2-<i>d</i>]- AND 4-AMINOTHIENO[3,4-<i>d</i>]PYRIMIDINES

Abstract

A study was carried out on the nucleophilic cleavage of the lactam bond in 4-amino(pyrrolidino, piperidino, morpolino)thieno[2,3-d]-, -[3,2-d]-, and -[3,4-d]pyrimido[1,2-b]isoquinolin-11-ones. This bond is readily cleaved upon heating in methanolic NaOH at reflux for 1-2 h to give previously unreported 4-amino-2-(o-carboxyphenylmethyl)thienopyrimidines. Replacement of the amine group by an OH group is possible under the reaction conditions, leading to the corresponding, already reported 2-(o-carboxyphenylmethyl)-4-oxothienopyrimidines. Prolonged refluxing (8-12 h) resulted in oxothienopyrimidines as the major products of the transformations of all the thienopyrimido-isoquinolinones studied. Biological activity predictions of these new products were compared in silico.

Author: A. V. Zadorozhny.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (7), pp 1028-1032

http://link.springer.com/article/10.1007/s10593-012-1095-y