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

页码：13185 / 13196

页数：12

共 21 条

[1] AROMATIC SUBSTITUTION .26. ALKALINE FERRICYANIDE OXIDATION OF PYRIDINIUM SALTS - EFFECTS OF SUBSTITUENTS AND MECHANISM [J].