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One-Pot Synthesis of 1,2-Disubstituted 4‑, 5‑, 6‑, and 7‑Azaindoles from Amino‑o‑halopyridines via N‑Arylation/Sonogashira/Cyclization Reaction

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journal contribution
posted on 15.09.2017, 17:20 authored by Sara I. Purificação, Marina J. D. Pires, Rafael Rippel, A. Sofia Santos, M. Manuel B. Marques
A direct synthesis of several 1,2-disubstituted 4-, 5-, 6-, and 7-azaindoles from available amino-o-halopyridines is described. This procedure involves a palladium-catalyzed N-arylation followed by a Sonogashira reaction and subsequent cyclization in a one-pot manner, exhibiting a wide scope and compatibility with electron-withdrawing and electron-donating groups. The strategy represents an advancement in azaindole chemistry with a straightforward approach toward 1,2-disubstituted azaindoles, while avoiding complex N-arylations of hindered 2-substituted azaindoles and difficult purification steps of intermediates.