Synthesis

Expedient synthesis of 5, 6-dihydroxyindole and derivatives via an improved Zn (II)-assisted 2, β-dinitrostyrene approach

L Novellino, M d'Ischia, G Prota

文献索引：Novellino, Luisa; D'Ischia, Marco; Prota, Giuseppe Synthesis, 1999 , # 5 p. 793 - 796

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被引用次数: 25

摘要

Abstract: A facile 3-step synthesis of 5, 6-dihydroxyindole (4a) is reported, featuring the Zn (II)-controlled regioselective nitration of 3, 4-dihydroxynitrostyrene (2) with tetranitromethane at pH 8.0, and the reductive cyclization of the resulting 4, 5-dihydroxy-2, b-dinitrostyrene (3a) with Na2S2O4/Zn (II) at pH 4. The latter procedure was successfully extended to the conversion of the 2, b-dinitrostyrenes 3b and 3c to 5, 6-dibenzyloxyindole (4b) and 5, 6- ...