Novel Syntheses of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-Benzothiazin-3(4H)-ones

Novel Syntheses of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-Benzothiazin-3(4H)-ones

Nucleophilic additions of α-mercaptoalkanoate esters and β-mercaptoalkanoate acids to benzoquinone diimines, followed by cyclization with trifluoroacetic acid or 1,3-dicyclohexylcarbodiimide (DCC), provide novel, high-yielding syntheses of 2H-1,4-benzothiazin-3(4H)-ones (3a − f) and 2,3-dihydro-1,5-...

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Veröffentlicht in:Journal of organic chemistry 2001-10, Vol.66 (20), p.6792-6796
Hauptverfasser: Katritzky, Alan R, Odens, Herman H, Zhang, Suoming, Rostek, Charles J, Maender, Otto W
Format: Artikel
Sprache:eng
Schlagworte:
Calcium Channel Blockers - chemical synthesis
Calcium Channel Blockers - chemistry
Magnetic Resonance Spectroscopy
Thiazepines - chemical synthesis
Thiazepines - chemistry
Thiazines - chemical synthesis
Thiazines - chemistry
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Zusammenfassung:Nucleophilic additions of α-mercaptoalkanoate esters and β-mercaptoalkanoate acids to benzoquinone diimines, followed by cyclization with trifluoroacetic acid or 1,3-dicyclohexylcarbodiimide (DCC), provide novel, high-yielding syntheses of 2H-1,4-benzothiazin-3(4H)-ones (3a − f) and 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones (5a − c), respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0101959