Synthesis and Chemical Reactivity of 5-Methoxy-2-vinyl-4-azaindoles

2-Vinyl-4-azaindoles are less reactive with dienophiles than 2-vinylindoles. 5-Methoxy-2-vinyl-4-azaindole 2a and its 1-methyl derivative 2a reacts with N-phenylmaleimide to yield cycloadducts only under vigorous conditions. 2b produces a cycloadduct with dimethyl acetylenedicarboxylate, while 2a yi...

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Bibliographic Details
Published in:Synthetic communications 1997-04, Vol.27 (8), p.1439-1447
Main Authors: Rodriguez-Salvador, Lourdes, Zaballos-Garcia, Elena, Gonzalez-Rosende, Eugenia, Sidi, Mohamed Djebouri, Sepúlveda-Arques, José, Jones, R. Alan
Format: Article
Language:English
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Summary:2-Vinyl-4-azaindoles are less reactive with dienophiles than 2-vinylindoles. 5-Methoxy-2-vinyl-4-azaindole 2a and its 1-methyl derivative 2a reacts with N-phenylmaleimide to yield cycloadducts only under vigorous conditions. 2b produces a cycloadduct with dimethyl acetylenedicarboxylate, while 2a yields a Michael-type adduct. Reactions with more reactive dienophiles gave only polymeric products.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919708006075