New isomers of 4,1-benzothiazepines. The first evidence for the desmotropy of seven-membered heterocycles

P. Csomós, L. Fodor, Jari Sinkkonen, Kalevi Pihlaja, G. Bernáth

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A novel procedure was developed for the preparation of 2,3-disubstituted 4,1-benzothiazepines, via the ring transformation of (2R*,2aS*)-2-chloro-2a-phenyl-2,2a-dih ydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-one (1) with sodium ethoxide in ethanol. The tautomeric products (R*)-3-ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothi azepine (4) and 3-ethoxycarbonyl-2-phenyl-1,5-dihydro-4,1-benzothiazepine (5) exhibit the rare phenomenon of desmotropy of the condensed seven-membered heterocycles. Surprisingly, these desmotropes could be separated by column chromatography. The products are unexpectedly stable in solution and their structures were proved by means of NMR and mass spectrometry.

Original languageEnglish
Pages (from-to)5665-5667
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number32
DOIs
Publication statusPublished - Aug 7 2006

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Azepines
Column chromatography
Isomers
Mass spectrometry
Chromatography
Mass Spectrometry
Ethanol
Nuclear magnetic resonance
sodium ethoxide
Product R

Keywords

  • β-Lactam
  • 4,1-Benzothiazepine
  • Desmotropy
  • Ring transformation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New isomers of 4,1-benzothiazepines. The first evidence for the desmotropy of seven-membered heterocycles. / Csomós, P.; Fodor, L.; Sinkkonen, Jari; Pihlaja, Kalevi; Bernáth, G.

In: Tetrahedron Letters, Vol. 47, No. 32, 07.08.2006, p. 5665-5667.

Research output: Contribution to journalArticle

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AU - Pihlaja, Kalevi

AU - Bernáth, G.

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AB - A novel procedure was developed for the preparation of 2,3-disubstituted 4,1-benzothiazepines, via the ring transformation of (2R*,2aS*)-2-chloro-2a-phenyl-2,2a-dih ydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-one (1) with sodium ethoxide in ethanol. The tautomeric products (R*)-3-ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothi azepine (4) and 3-ethoxycarbonyl-2-phenyl-1,5-dihydro-4,1-benzothiazepine (5) exhibit the rare phenomenon of desmotropy of the condensed seven-membered heterocycles. Surprisingly, these desmotropes could be separated by column chromatography. The products are unexpectedly stable in solution and their structures were proved by means of NMR and mass spectrometry.

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