AN UNEXPECTED [2+2]-CYCLOADDITION REACTION OF 4-METHYLDITHIENO-[3,4-B-3',2'-D]PYRIDINIUM IODIDE WITH DIMETHYL ACETYLENEDICARBOXYLATE

被引：5
作者：
TEMCIUC, E [1 ]
HORNFELDT, AB [1 ]
GRONOWITZ, S [1 ]
STALHANDSKE, C [1 ]
机构：
[1] LUND UNIV,CTR CHEM,S-22100 LUND,SWEDEN
来源：
TETRAHEDRON | 1995年 / 51卷 / 48期
关键词：
D O I：
10.1016/0040-4020(95)00789-B
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unexpected [2+2]-cycloaddition occured in the reaction of 4-methyldithieno-[3,4-b:3',2'-d]pyridinium iodide (3)with two equivalents of DMAD, giving 4-(trans-1,2-dicarbomethoxy-2-iodovinyl)-5-methyl-6,7-dicarbomethoxy-4,5-dihydrothieno[2,3-c]quinoline (4) in 54 % yield. 4 is formed via 4-methyl-5-(trans-1,2-dicarbomethoxy-2-iodo-4,5-dihydrothieno[3,4-b: 3',2'-d] pyridine (16), followed by [2+2]-cycloaddition. The primary adduct rearranges via a thiepin to an episulfide which eliminates sulfur to give 4.
引用
收藏
页码：13185 / 13196
页数：12
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