Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines.
2-(Bromomethyl)-1-sulfonylaziridines were converted into novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines upon treatment with 2-aminothiophenol in THF in the presence of K2CO3. Starting from 3-substituted 2-(sulfonyloxymethyl)aziridines, a regio- and stereocontrolled synthesis of trans-2-phenyl- and trans-4-(phenyl or propyl)-3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines was developed in good yields via two different reaction pathways, depending on the nature of the sulfonyloxy group.
Karikomi
Michinori
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium.
D'hooghe
Matthias
M
Verniest
Guido
G
De Kimpe
Norbert
N
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
C106746:1,5-benzothiazepine; D001388:Aziridines; D013841:Thiazepines