An unexpected isomerization of 1,3-benzothiazine and isoquinoline-condensed β-lactams

Research output: Article

7 Citations (Scopus)

Abstract

A series of novel aryl-substituted β-lactams condensed with 1,3-benzothiazines, isoquinolines or 1,4-benzothiazepine were obtained by means of the Staudinger reaction and isomerized in the presence of sodium methoxide to the thermodynamically more stable form. The structures of the new molecules were determined by NMR spectroscopy. Theoretical calculations corroborate the experimentally observed structure-reactivity relationships.

Original languageEnglish
Pages (from-to)54-61
Number of pages8
JournalJournal of Molecular Structure
Volume983
Issue number1-3
DOIs
Publication statusPublished - nov. 1 2010

Fingerprint

Isoquinolines
Lactams
Isomerization
Nuclear magnetic resonance spectroscopy
Methanol
Molecules
isoquinoline

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

@article{48ee863da3fd4920afd12cd1044fb7b7,
title = "An unexpected isomerization of 1,3-benzothiazine and isoquinoline-condensed β-lactams",
abstract = "A series of novel aryl-substituted β-lactams condensed with 1,3-benzothiazines, isoquinolines or 1,4-benzothiazepine were obtained by means of the Staudinger reaction and isomerized in the presence of sodium methoxide to the thermodynamically more stable form. The structures of the new molecules were determined by NMR spectroscopy. Theoretical calculations corroborate the experimentally observed structure-reactivity relationships.",
keywords = "Cis-trans-β-lactams, DFT analysis, Isoquinoline, NMR spectroscopy, Staudinger reaction, Sulfur nitrogen heterocycles",
author = "L. Fodor and P. Csom{\'o}s and F. F{\"u}l{\"o}p and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2010",
month = "11",
day = "1",
doi = "10.1016/j.molstruc.2010.08.030",
language = "English",
volume = "983",
pages = "54--61",
journal = "Journal of Molecular Structure",
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TY - JOUR

T1 - An unexpected isomerization of 1,3-benzothiazine and isoquinoline-condensed β-lactams

AU - Fodor, L.

AU - Csomós, P.

AU - Fülöp, F.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2010/11/1

Y1 - 2010/11/1

N2 - A series of novel aryl-substituted β-lactams condensed with 1,3-benzothiazines, isoquinolines or 1,4-benzothiazepine were obtained by means of the Staudinger reaction and isomerized in the presence of sodium methoxide to the thermodynamically more stable form. The structures of the new molecules were determined by NMR spectroscopy. Theoretical calculations corroborate the experimentally observed structure-reactivity relationships.

AB - A series of novel aryl-substituted β-lactams condensed with 1,3-benzothiazines, isoquinolines or 1,4-benzothiazepine were obtained by means of the Staudinger reaction and isomerized in the presence of sodium methoxide to the thermodynamically more stable form. The structures of the new molecules were determined by NMR spectroscopy. Theoretical calculations corroborate the experimentally observed structure-reactivity relationships.

KW - Cis-trans-β-lactams

KW - DFT analysis

KW - Isoquinoline

KW - NMR spectroscopy

KW - Staudinger reaction

KW - Sulfur nitrogen heterocycles

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U2 - 10.1016/j.molstruc.2010.08.030

DO - 10.1016/j.molstruc.2010.08.030

M3 - Article

VL - 983

SP - 54

EP - 61

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - 1-3

ER -