ISSN:
1434-4475
Keywords:
Keywords. Benzofuro-annelated 1,5-benzothiazepines; 4,5-Dihydro-1,5-benzothiazepines; 2,3,4,5-Tetrahydro-1,5-benzothiazepines; Cyclocondensation; Regiochemistry; Stereochemistry; Conformational analysis.
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary. A convenient procedure is reported for the preparation of benzofuro-annelated 2-phenyl-1,5-benzothiazepine derivatives by oxidative cyclocondensation of phenolic β-diketones with o-aminothiophenol in DMSO. The regiochemistry of these compounds is proven by HMBC signals and the existence of a five-bond 19F,13C-2 coupling. Surprisingly, treatment with LiAlH4 at room temperature led to a double reduction under opening of the five-membered ring. Refluxing such solutions with a higher amount of LiAlH4 gave rise to a further reduced derivative possessing the trans-configuration. All structures (regio- and stereochemistry) were assigned on the basis of NMR spectroscopic data.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/s007060050320
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