A facile approach for synthesis of thiazines-, thiazoles- and triazoles-annulated 6-styryl-2-thiouracil derivative

Utility of 4-oxo-6-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 1 in synthesis of a new series of fused pyrimidines was described. Pyrimido[2,1- b ][1,3]thiazines 6 – 9 were obtained via Michael addition of compound 1 to the polarized systems 2 – 5 in the presence of nanosized ZnO. S...

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Bibliographic Details
Published in:Journal of the Iranian Chemical Society 2020, Vol.17 (1), p.119-125
Main Authors: Morsy, H. A., Moustafa, A. H.
Format: Article
Language:English
Subjects:
Alkylation
Analytical Chemistry
Biochemistry
Carbon disulfide
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chlorides
Chloroacetic acid
Formic acid
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Pyrimidines
Thiouracil derivatives
Triazoles
Zinc oxide
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Summary:Utility of 4-oxo-6-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 1 in synthesis of a new series of fused pyrimidines was described. Pyrimido[2,1- b ][1,3]thiazines 6 – 9 were obtained via Michael addition of compound 1 to the polarized systems 2 – 5 in the presence of nanosized ZnO. S -alkylation of pyrimidine 1 followed by cyclization with phenacyl bromide, monochloroacetic acid, chloroacetonitrile and oxalyl chloride afforded the desired thiazolo[3,2- a ]pyrimidines 10 – 13 . Hydrazinolysis of compound 1 followed by addition cyclization with acetic anhydride, formic acid, carbon disulfide and benzoyl chloride afforded triazolo[4,3- a ]pyrimidines 15 – 18 . The antimicrobial screening showed high activity for thiazolo[3,2- a ]pyrimidines 11 and 12 against both Gram (+ ve) and Gram (− ve) bacteria.
ISSN:1735-207X
1735-2428
DOI:10.1007/s13738-019-01760-w