Novel syntheses of 2,3-dihydro-1,5-benzothiazepin-4(5h)-ones and 2h-1,4-benzothiazin-3(4h)-ones.
Nucleophilic additions of alpha-mercaptoalkanoate esters and beta-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.
Katritzky
A R
AR
Flexsys America L. P., 260 Springside Drive, Akron, Ohio 44333, USA. katritzky@chem.ufl.edu
Odens
H H
HH
Zhang
S
S
Rostek
C J
CJ
Maender
O W
OW
D002121:Calcium Channel Blockers / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
D002121:Calcium Channel Blockers; D013841:Thiazepines; D013843:Thiazines