Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Optically active 1,5-benzothiazepin-4-ones by ring transformation of 5-ylidene-1,3-dioxan-4-ones with 2-aminothiophenol

Akbar Ali,b   Viqar Uddin Ahmad,b   Joachim Leistnera  and  Jürgen Liebscher*a  

* Corresponding authors

a Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1–2, Berlin, Germany

b International Centre for Chemical Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi, Pakistan

Abstract

Optically active cis- and trans-3-(1-hydroxyethyl)-1,5-benzothiazepin-4-ones 4 and 5 have been synthesised by ring transformation of (E )- and (Z )-5-ylidene-1,3-dioxan-4-ones 1 with 2-aminothiophenol. Stereoselective conjugate addition of the –SH group of 2-aminothiophenol to the Michael system of the chiral 5-ylidene-1,3-dioxan-4-one 1, catalysed by BuLi, gave adducts 2 and 3. The stereochemical mode of attack can be rationalised by hydrogen bonding of the attacking 2-aminothiophenolate with the oxygen atoms of the dioxanone ring. Treatment of the adducts 2 and 3 with ethylmagnesium bromide afforded ring transformation by attack of the amino group at the carbonyl carbon atom cleaving the dioxanone ring. The resulting 3-(1-hydroxyethyl)-1,5-benzothiazepin-4-ones 4 and 5 represent structural analogues of Diltiazem®, a widely used drug in the treatment of hypertension.

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Article information

DOI
https://doi.org/10.1039/B001928N
Article type
Paper
Submitted
09 Mar 2000
Accepted
18 Apr 2000
First published
01 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1897-1902

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Optically active 1,5-benzothiazepin-4-ones by ring transformation of 5-ylidene-1,3-dioxan-4-ones with 2-aminothiophenol

A. Ali, V. Uddin Ahmad, J. Leistner and J. Liebscher, J. Chem. Soc., Perkin Trans. 1, 2000, 1897 DOI: 10.1039/B001928N

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