Synthesis, reactions, and antimicrobial evaluations of new benzothiazine derivatives

4H‐Spiro[benzo[d][1,3]oxathiine‐2,1′‐cyclohexan]‐4‐one undergoes aminolysis with certain aromatic amines to give the respective 4‐benzenesulfonamide, Ethyl benzoate, and 4‐acetylphenyl of 4‐oxospirobenzo[e][1,3]thiazine derivatives. The Schiff bases prepared by reacting Ethyl benzoate derivative 2a...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2020-01, Vol.57 (1), p.163-172
Main Authors: Ewies, Ewies F, Fatma AA El‐Hag
Format: Article
Language:English
Subjects:
Aldehydes
Amines
Antiinfectives and antibacterials
Antimicrobial agents
Benzoates
Chemical synthesis
Hydrazines
Imines
Isocyanates
Reagents
Thiourea derivatives
Urea
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Summary:4H‐Spiro[benzo[d][1,3]oxathiine‐2,1′‐cyclohexan]‐4‐one undergoes aminolysis with certain aromatic amines to give the respective 4‐benzenesulfonamide, Ethyl benzoate, and 4‐acetylphenyl of 4‐oxospirobenzo[e][1,3]thiazine derivatives. The Schiff bases prepared by reacting Ethyl benzoate derivative 2a with aldehydes, undergoes cyclocondensation with thioglycolic acid yielding p‐methoxyphenyl and 2‐(thiophen‐2‐yl) thiazolidinone derivatives. Treatment of the benzoate derivative with hydrazine hydrate afforded the corresponding benzohydrazide derivative which upon reaction with phenyl isocyanate and phenyl isothiocyanate afforded the urea and thiourea derivatives. New pyrimidine, pyridone, and imino pyridine derivatives of 4‐oxospirobenzo[e][1,3]thiazine were also successfully prepared by reacting 2b or 2c with the appropriate organic reagents. Structural elucidations for the new products were based upon compatible microanalytical and spectroscopic measurements. Besides, their biological screening indicated that they possess potent antimicrobial activity in comparison with reference drugs.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3759