Synthesis of Substituted Thienopyrimidinones Based on 2-Amino-4-(1,4-benzodioxan-2-yl) Thiophene-3-carboxylic Acid Ethyl Ester

Svetlana O. Vardanyan; Вартанян Светлана Ониковна; Alina S. Avagyan; Авакян Алина Суреновна; Amalya B. Sargsyan; Саргсян Амаля Багратовна; Seda A. Harutyunyan; Арутюнян Седа Арутюновна; Hrachik V. Gasparyan; Гаспарян Грачик Ваграмович; Asya A. Aghekyan; Агекян Aся Aгековна

doi:10.31857/S0514749225040109

Synthesis of Substituted Thienopyrimidinones Based on 2-Amino-4-(1,4-benzodioxan-2-yl) Thiophene-3-carboxylic Acid Ethyl Ester

Authors: Vardanyan S.O.¹, Avagyan A.S.¹, Sargsyan A.B.¹, Harutyunyan S.A.¹, Gasparyan H.V.¹, Aghekyan A.A.¹
Affiliations:
1. Scientific Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia
Issue: Vol 61, No 4 (2025)
Pages: 447-452
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://ruspoj.com/0514-7492/article/view/689667
DOI: https://doi.org/10.31857/S0514749225040109
EDN: https://elibrary.ru/SEAFNB
ID: 689667

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Abstract

The previously obtained N-arylamides of 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylic acid ethyl ester were cyclized to 2-aryl-substituted 3-aminothienopyrimidin-4-ones by the action of hydrazine hydrate. By condensation of the starting amino ester with chloroacetic acid chloride was obtained chloramide, which was converted by the action of piperidine and morpholine into the corresponding aminomethylamides. The latters were also subjected to cyclization with hydrazine hydrate to 3-aminothienopyrimidin-4-one derivatives with aminomethyl substituents in the second position. The antihypoxic activity of the synthesized compounds was studied.

Keywords

1,4-benzodioxane, chloramide, 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylic acid ethyl ester, thienopyrimidin-4-one, cyclization

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