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Updated: Feb 22, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
One-Pot Synthesis of 1,2-Disubstituted 4-, 5-, 6-, and 7-Azaindoles from Amino-o-halopyridines via
Sara I Purificação1, Marina J D Pires1, Rafael Rippel1
1LAQV@REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa , Campus de Caparica, 2829-516 Caparica, Portugal.
Abstract:
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.
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