Ring transformations of β-lactam-condensed 1,3-benzothiazines to isoquinoline and thiazole derivatives by sulfur extrusion and addition sequences

被引：4
|
作者：
Fodor, Lajos [1 ,2 ,3 ]
Csomos, Peter [1 ,2 ,3 ]
Csampai, Antal [4 ]
Sohar, Pal [4 ]
机构：
[1] Szent Istvan Univ, Inst Hlth Care & Environm Sanitat Studies, H-5700 Gyula, Hungary
[2] Cty Hosp, Cent Lab, H-5701 Gyula, Hungary
[3] Univ Szeged, Inst Pharmaceut Chem, Res Grp Stereochem, Hungarian Acad Sci, H-6720 Szeged, Hungary
[4] Eotvos Lorand Univ, Inst Chem, H-1518 Budapest, Hungary
来源：
TETRAHEDRON | 2012年 / 68卷 / 32期
关键词：
Ring transformation; Dichloro-beta-lactam; 1,3-Benzothiazine; Isoquinoline; Benzothiazepine; Thiazole; BUILDING-BLOCKS; STEREOSELECTIVE-SYNTHESIS; INHIBITORS; HETEROCYCLES; EXPANSION;
D O I：
10.1016/j.tet.2012.05.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The ring transformations of dichloro-P-lactam-fused 2-aryl-1,3-benzothiazines with sodium methoxide were investigated. With 2 equiv of base, the dichloro-beta-lactam derivatives underwent rearrangement and dihydro-1,4-benzothiazepines, 3,4-substituted isoquinolines and substituted thiazole disulfides were isolated. A possible reaction mechanism is proposed for the simultaneous formation of the novel products. The formation of isoquinoline and thiazole derivatives can be explained by sulfur extrusion and addition sequences. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6581 / 6586
页数：6
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