Synthesis and activity of 5-(aminomethyl)-1, 3-cyclohexanediones: enolic analogs of. gamma.-aminobutyric acid

…, R Schlichter, M Desarmenien, P Feltz…

Index: Mann; Humblet; Chambon; Schlichter; Desarmenien; Feltz; Wermuth Journal of Medicinal Chemistry, 1985 , vol. 28, # 10 p. 1440 - 1446

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Citation Number: 7

Abstract

Method A. As outlined in Scheme I either 3, 5-dimethoxybenzamide (2) or 3, 4, 5- trimethoxybenzamide (3) gave rise to the same compound: 3-carbamoyl-1, Ei-di-methoxy-l, 4-cyclohexadiene (4) when submitted to a Birch reduction under classical conditions. 12 A further reduction of the carboxamide 4 with lithium aluminum hydride (LAH) in tetrahydrofuran led to an approximate 1: l mixture of the expected 3-(aminomethyl)-l, 5- ...

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