Investigation of ring transformations of diaryl-β-lactams condensed with 1,3-benzothiazines

Research output: Article

1 Citation (Scopus)

Abstract

Reactions of derivatives of the isoquinoline analog trans-2,2a-diaryl-2,2a- dihydro-5,6- dimethoxy-1H,8H-azeto[2,1-b][1,3]benzothiazin-1-one were studied under basic conditions. Their treatment with sodium methoxide in methanol resulted first in alcoholysis of the β-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding β-amino acid derivatives, disulfides of N-(ortho- mercaptobenzyl)- substituted diaryl-3-aminoacrylic acid methyl esters, were obtained in good yields. The structures of the new molecules were proved by means of NMR and IR spectroscopy. Geometric isomerism investigations indicated the presence of the Z forms of the acrylic acid moiety.

Original languageEnglish
Pages (from-to)37-46
Number of pages10
JournalArkivoc
Volume2012
Issue number5
Publication statusPublished - 2012

Fingerprint

Lactams
Disulfides
Methanol
Thiazines
Derivatives
Sulfhydryl Compounds
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Esters
Amino Acids
Oxidation
Molecules
Acids
acrylic acid
isoquinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

@article{7874d524542446f0a64342ffc8383b97,
title = "Investigation of ring transformations of diaryl-β-lactams condensed with 1,3-benzothiazines",
abstract = "Reactions of derivatives of the isoquinoline analog trans-2,2a-diaryl-2,2a- dihydro-5,6- dimethoxy-1H,8H-azeto[2,1-b][1,3]benzothiazin-1-one were studied under basic conditions. Their treatment with sodium methoxide in methanol resulted first in alcoholysis of the β-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding β-amino acid derivatives, disulfides of N-(ortho- mercaptobenzyl)- substituted diaryl-3-aminoacrylic acid methyl esters, were obtained in good yields. The structures of the new molecules were proved by means of NMR and IR spectroscopy. Geometric isomerism investigations indicated the presence of the Z forms of the acrylic acid moiety.",
keywords = "β-amino acid, β-lactam, 1 3-Benzothiazine, 3-aminoacrylic acid, Aring opening, Disulfide",
author = "L. Fodor and P. Csom{\'o}s and Benedek K{\'a}rolyi and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2012",
language = "English",
volume = "2012",
pages = "37--46",
journal = "Arkivoc",
issn = "1551-7012",
publisher = "Arkat USA",
number = "5",

}

TY - JOUR

T1 - Investigation of ring transformations of diaryl-β-lactams condensed with 1,3-benzothiazines

AU - Fodor, L.

AU - Csomós, P.

AU - Károlyi, Benedek

AU - Csámpai, A.

AU - Sohár, P.

PY - 2012

Y1 - 2012

N2 - Reactions of derivatives of the isoquinoline analog trans-2,2a-diaryl-2,2a- dihydro-5,6- dimethoxy-1H,8H-azeto[2,1-b][1,3]benzothiazin-1-one were studied under basic conditions. Their treatment with sodium methoxide in methanol resulted first in alcoholysis of the β-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding β-amino acid derivatives, disulfides of N-(ortho- mercaptobenzyl)- substituted diaryl-3-aminoacrylic acid methyl esters, were obtained in good yields. The structures of the new molecules were proved by means of NMR and IR spectroscopy. Geometric isomerism investigations indicated the presence of the Z forms of the acrylic acid moiety.

AB - Reactions of derivatives of the isoquinoline analog trans-2,2a-diaryl-2,2a- dihydro-5,6- dimethoxy-1H,8H-azeto[2,1-b][1,3]benzothiazin-1-one were studied under basic conditions. Their treatment with sodium methoxide in methanol resulted first in alcoholysis of the β-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding β-amino acid derivatives, disulfides of N-(ortho- mercaptobenzyl)- substituted diaryl-3-aminoacrylic acid methyl esters, were obtained in good yields. The structures of the new molecules were proved by means of NMR and IR spectroscopy. Geometric isomerism investigations indicated the presence of the Z forms of the acrylic acid moiety.

KW - β-amino acid

KW - β-lactam

KW - 1 3-Benzothiazine

KW - 3-aminoacrylic acid

KW - Aring opening

KW - Disulfide

UR - http://www.scopus.com/inward/record.url?scp=84855696743&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84855696743&partnerID=8YFLogxK

M3 - Article

VL - 2012

SP - 37

EP - 46

JO - Arkivoc

JF - Arkivoc

SN - 1551-7012

IS - 5

ER -