Synthesis of New 5-(1,4-Benzodioxan-2-yl)thieno[2,3-d]pyrimidine Derivatives

Cyclization of previously synthesized ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carbox­ylate with formamide gave 5-(1,4-benzodioxan-2-yl)thieno[2,3- d ]pyrimidin-4(3 H )-one which was treated with phosphoryl chloride in pyridine to obtain the corresponding 4-chloro derivative. The latter rea...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2022-07, Vol.58 (7), p.977-981
Main Authors: Vardanyan, S. O., Aghekyan, A. A., Avagyan, A. S., Sargsyan, A. B., Panosyan, H. A., Harutyunyan, S. A., Gasparyan, H. V.
Format: Article
Language:English
Subjects:
Amines
Chemistry
Chemistry and Materials Science
Formic acid
Hydrazines
Organic Chemistry
Pyrimidines
Synthesis
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Summary:Cyclization of previously synthesized ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carbox­ylate with formamide gave 5-(1,4-benzodioxan-2-yl)thieno[2,3- d ]pyrimidin-4(3 H )-one which was treated with phosphoryl chloride in pyridine to obtain the corresponding 4-chloro derivative. The latter reacted with various primary and secondary amines to produce a series of new thieno[2,3- d ]pyrimidines containing a pharmacophoric fragment at the 4-position. The reaction of 5-(1,4-benzodioxan-2-yl)-4-chlorothieno[2,3- d ]pyrimidine with hydrazine hydrate afforded the corresponding 4-hydrazinyl derivative which was cyclized with formic acid to thieno[3,2- e ][1,2,4]triazolo[1,5- c ]pyrimidine derivative. Antihypoxic properties of the synthesized compounds were studied.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022070053