Palladium-catalyzed synthesis of 2,3-disubstituted 5-azaindoles via heteroannulation reaction and of 2-substituted 5-azaindoles through domino sila-Sonogashira/5-endo cyclization

The Journal of Organic Chemistry
Marion LivecchiFrédéric Schmidt

Abstract

A general and efficient procedure for the synthesis of 2,3-disubstituted 5-azaindoles through the palladium-catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diaryl-, dialkyl-, or arylalkylalkynes is described along with a study of the reaction regioselectivity. The preparation of 2-monosubstituted 5-azaindoles via sila-Sonogashira/5-endo cyclization is also reported. These methods allowed us to prepare 36 diversely substituted 5-azaindoles in good yields.

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Citations

Jun 25, 2013·Chemical Reviews·Rafael Chinchilla, Carmen Nájera
Jul 2, 2016·Chemical Communications : Chem Comm·Hayden A SharmaKarl A Scheidt
Mar 19, 2014·Organic & Biomolecular Chemistry·Anita JanigaDaniel T Gryko
Jun 15, 2019·Organic Letters·Shalini VermaAkhilesh K Verma
Nov 28, 2013·The Journal of Organic Chemistry·Nared PhetrakPitak Chuawong

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