A Convenient Synthesis of 1,4-Benzothiazepines from 1,3-Benzothiazines via the Ring Transformation of beta-Lactam-Condensed 1,3-Benzothiazine Derivatives

A convenient synthesis was devised for rare 2,3-disubstituted 4,5-dihydro-1,4-benzothiazepines from 2-aryl-4H-1,3-benzothiazines. The Staudinger reaction of 1,3-benzothiazines obtained with chloroacetyl chloride selectively furnished trans-monochloro-beta-lactam-condensed thiazines. The ring expansi...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 17; pp. 2943 - 2948
Main Authors Fodor, Lajos, Csomos, Peer, Csampai, Antal, Sohar, Pal
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,4-benzothiazepine
SATURATED HETEROCYCLES
CYCLOADDITION
beta-lactams
ring expansion
1,3-benzothiazine
S,N-heterocycles
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Summary:A convenient synthesis was devised for rare 2,3-disubstituted 4,5-dihydro-1,4-benzothiazepines from 2-aryl-4H-1,3-benzothiazines. The Staudinger reaction of 1,3-benzothiazines obtained with chloroacetyl chloride selectively furnished trans-monochloro-beta-lactam-condensed thiazines. The ring expansion of azeto[2,1-b][1,3]benzothiazin-1-one derivatives with sodium methoxide afforded 1,4-benzothiazepines as the sole product in good yields. The structures of the new molecules were proved by means NMR and IR spectroscopy.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1258155