Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate

Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3- d ]pyrimidin-4(1 H )-ones by the action of hydrazine hydrate. The con­densation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chlo...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2024-03, Vol.60 (3), p.397-402
Main Authors: Vardanyan, S. O., Avagyan, A. S., Sargsyan, A. B., Harutyunyan, S. A., Gasparyan, H. V., Aghekyan, A. A.
Format: Article
Language:English
Subjects:
Carboxylates
Chemistry
Chemistry and Materials Science
Hydrazines
Organic Chemistry
Piperidine
Substitutes
Synthesis
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Summary:Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3- d ]pyrimidin-4(1 H )-ones by the action of hydrazine hydrate. The con­densation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-amino­thienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428024030047