A Convenient Synthesis of 1,4-Benzothiazepines from 1,3-Benzothiazines via the Ring Transformation of β-Lactam-Condensed 1,3-Benzothiazine Derivatives

被引：18

作者：

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

Csomos, Peer ^{[1
,2
,3
]}

Csampai, Antal ^{[4
]}

Sohar, Pal ^{[4
,5
,6
]}

机构：

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

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

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

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

[5] Hungarian Acad Sci, Prot Modelling Res Grp, H-1518 Budapest, Hungary

[6] Eotvos Lorand Univ, H-1518 Budapest, Hungary

来源：

SYNTHESIS-STUTTGART | 2010年 / 17期

关键词：

1,4-benzothiazepine; 1,3-benzothiazine; beta-lactams; ring expansion; S; N-heterocycles; SATURATED HETEROCYCLES; CYCLOADDITION;

D O I：

10.1055/s-0030-1258155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-beta-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.

引用

页码：2943 / 2948

页数：6

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