Novel β-lactam condensed 3-thiaquinolines: an efficient synthesis and structural characterization

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

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Quinoline analog 2-aryl-4H-3,1-benzothiazine derivatives 8-13, obtained by the condensation of o-aminobenzyl chloride 1 with substituted thiobenzamides 2-7, were transformed to azeto[2,1-a][3,1]benzothiazin-1-one derivatives 18-23a,b,c and 24d,e by reaction with the corresponding substituted acetyl chlorides 14-17 in the presence of triethylamine. The structures of the new molecules were determined by NMR spectroscopy and electron ionization (EI) mass spectrometry. The typical EI+ mass spectrometric fragmentations of 8-13 and 18-23a,b,c and 24d,e are discussed in detail.

Original languageEnglish
Pages (from-to)1002-1011
Number of pages10
JournalTetrahedron
Volume64
Issue number6
DOIs
Publication statusPublished - Feb 4 2008

Fingerprint

Lactams
Ionization
Electrons
Derivatives
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Chlorides
Condensation
Mass Spectrometry
Magnetic Resonance Spectroscopy
Molecules
triethylamine
acetyl chloride
quinoline
thiobenzamide

Keywords

  • β-Lactams
  • Mass spectrometry
  • NMR spectroscopy
  • Sulfur, nitrogen heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel β-lactam condensed 3-thiaquinolines : an efficient synthesis and structural characterization. / Csomós, P.; Fodor, L.; Bernáth, G.; Sinkkonen, Jari; Salminen, Jari; Wiinamäki, Kirsti; Pihlaja, Kalevi.

In: Tetrahedron, Vol. 64, No. 6, 04.02.2008, p. 1002-1011.

Research output: Contribution to journalArticle

Csomós, P. ; Fodor, L. ; Bernáth, G. ; Sinkkonen, Jari ; Salminen, Jari ; Wiinamäki, Kirsti ; Pihlaja, Kalevi. / Novel β-lactam condensed 3-thiaquinolines : an efficient synthesis and structural characterization. In: Tetrahedron. 2008 ; Vol. 64, No. 6. pp. 1002-1011.
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AU - Salminen, Jari

AU - Wiinamäki, Kirsti

AU - Pihlaja, Kalevi

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