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

Hüseyin Cavdar; Nurullah Saraçoglu

doi:10.1021/jo061336f

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

J Org Chem. 2006 Sep 29;71(20):7793-9. doi: 10.1021/jo061336f.

Authors

Hüseyin Cavdar¹, Nurullah Saraçoglu

Affiliation

¹ Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.

PMID: 16995688
DOI: 10.1021/jo061336f

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbazoles / chemical synthesis*
Carbazoles / chemistry
Carboxylic Acids / chemistry
Indoles / chemistry
Molecular Structure
Vinyl Compounds / chemical synthesis*

Substances

Carbazoles
Carboxylic Acids
Indoles
Vinyl Compounds