The Journal of Organic Chemistry

Extension of the Nenitzescu reaction to a cyclic enamino ketone. One-step synthesis of 6-hydroxy-9H-pyrimido [4, 5-b] indole-2, 4-dione

JL Bernier, JP Henichart

Index: Bernier, Jean-Luc; Henichart, Jean-Pierre Journal of Organic Chemistry, 1981 , vol. 46, # 21 p. 4197 - 4198

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Citation Number: 37

Abstract

A new one-step synthesis of the 6-hydroxypyrimido [4, 5-b] indole ring involving the condensation of p-benzoquinone with 1, 3-dimethyl-6-aminouacil has been reported. This procedure, an extension of the Nenitzescu reaction, was compared to a more classical Fischer-type cyclization. In both reactions, intermediates have provided useful mechanistic information. When nitromethane was used as a solvent, this new Nenitzescu-type ...