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

被引：2

作者：

Fodor, Lajos ^{[1
,2
,3
,4
]}

Csomos, Peter ^{[1
,2
,3
,4
]}

Karolyi, Benedek ^{[5
]}

Csampai, Antal ^{[5
]}

Sohar, Pal ^{[5
]}

机构：

[1] Szent Istvan Univ, Inst Hlth Care & Environm Sanitat Studies, Szent Istvan St 17-19, H-5700 Gyula, Hungary

[2] Cty Hosp, Cent Lab, H-5701 Gyula, Hungary

[3] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[4] Hungarian Acad Sci, Res Grp Stereochem, H-6720 Szeged, Hungary

[5] Eotvos Lorand Univ, Inst Chem, H-1518 Budapest, Hungary

来源：

ARKIVOC | 2012年

关键词：

1,3-Benzothiazine; beta-lactam; beta-amino acid; 3-aminoacrylic acid; ring opening; disulfide; BUILDING-BLOCKS; AMINO ACIDS; DERIVATIVES; CYCLOADDITION;

D O I：

10.3998/ark.5550190.0013.505

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding beta-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.

引用

页码：37 / 46

页数：10

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