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

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 inves...

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Veröffentlicht in:	Journal of organic chemistry 2006-09, Vol.71 (20), p.7793-7799
Hauptverfasser:	CAVDAR, Hiiseyin, SARACOGLU, Nurullah
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbazoles - chemical synthesis Carbazoles - chemistry Carboxylic Acids - chemistry Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemistry Molecular Structure Noncondensed benzenic compounds Organic chemistry Preparations and properties Vinyl Compounds - chemical synthesis
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo061336f