Synthesis of new 2-vinylation products of indole via a michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles

被引：65
作者：
Cavdar, Huseyin [1 ]
Saracoglu, Nurullah [1 ]
机构：
[1] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 20期
关键词：
D O I：
10.1021/jo061336f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels-Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.
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页码：7793 / 7799
页数：7
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