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
收藏
页码：2943 / 2948
页数：6
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