Synthesis of 2-Aryl-1-hydroxyazaindoles and 2-Arylazaindoles via Oxidation of o-Hydroxyaminostyrylpyridines

D Kuzmich, C Mulrooney

Index: Kuzmich, Daniel; Mulrooney, Carol Synthesis, 2003 , # 11 p. 1671 - 1678

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Citation Number: 17

Abstract

Abstract 2-Aryl-1-hydroxyazaindoles (pyrrolopyridin-1-ols) are prepared via an oxidation/cyclization of o-hydroxyaminostyrylpyridines with DDQ. Reduction of the N-OH bond affords the corresponding 2-arylazaindoles (1H-pyrrolopyridines). The scope of the cyclization is explored via (i) the condensation of 4-methyl-3-nitropyridine with various aryl aldehydes to afford 2-aryl substituted 6-azaindoles and,(ii) the synthesis of 2-phenyl-4-, 5- ...