A convenient synthesis of 1,4-benzothiazepines from 1,3-benzothiazines via the ring transformation of -lactam-condensed 1,3-benzothiazine derivatives

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13 Citations (Scopus)

Abstract

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 β- 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.

Original languageEnglish
Article numberT07910SS
Pages (from-to)2943-2948
Number of pages6
JournalSynthesis
Issue number17
DOIs
Publication statusPublished - 2010

Fingerprint

Thiazines
Lactams
Nuclear magnetic resonance spectroscopy
Methanol
Infrared spectroscopy
Sodium
Derivatives
Molecules
chloroacetyl chloride

Keywords

  • -lactams
  • 1,3-benzothiazine
  • 1,4-benzothiazepine
  • ring expansion
  • S,N-heterocycles

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

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title = "A convenient synthesis of 1,4-benzothiazepines from 1,3-benzothiazines via the ring transformation of -lactam-condensed 1,3-benzothiazine derivatives",
abstract = "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 β- 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.",
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author = "L. Fodor and P. Csom{\'o}s and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2010",
doi = "10.1055/s-0030-1258155",
language = "English",
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journal = "Synthesis",
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publisher = "Georg Thieme Verlag",
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T1 - A convenient synthesis of 1,4-benzothiazepines from 1,3-benzothiazines via the ring transformation of -lactam-condensed 1,3-benzothiazine derivatives

AU - Fodor, L.

AU - Csomós, P.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2010

Y1 - 2010

N2 - 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 β- 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.

AB - 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 β- 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.

KW - -lactams

KW - 1,3-benzothiazine

KW - 1,4-benzothiazepine

KW - ring expansion

KW - S,N-heterocycles

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U2 - 10.1055/s-0030-1258155

DO - 10.1055/s-0030-1258155

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