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Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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  1. Enamine Ltd., 23 Aleksandra Matrosova St., Kyiv, 01103, Ukraine

    A. V. Zadorozhny

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  1. A. V. Zadorozhny
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Correspondence to A. V. Zadorozhny.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1107-1112, July, 2012.

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Zadorozhny, A.V. Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines. Chem Heterocycl Comp 48, 1028–1032 (2012). https://doi.org/10.1007/s10593-012-1095-y

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