Synthesis and Reactions of 2-Arylhydrazinotropones. II. Synthesis of 5-Aryltropolones and B-Ring-Open Colchicine Analogues via Benzidine Type Rearrangement of …

T Nozoe, K Takase, M Yasunami, M Ando…

Index: Nozoe, Tetsuo; Takase, Kahei; Yasunami, Masafumi; Ando, Masayoshi; Saito, Hiroaki; et al. Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 1 p. 128 - 142

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Citation Number: 11

Abstract

Treatment of a wide variety of 2-(2-arylhydrazino) tropones with ethanolic acid at 50–80° C readily gave the benzidine type rearrangement products, 2-amino-5-(4-aminoaryl) tropones, besides minor amounts of byproducts of various type. The main products were conveniently led to the corresponding 5-aryltropolones. Similarly, 2-(2-arylhydrazino) tropones bearing an isopropyl and isopropenyl group at the 4-position afforded 4-substituted 2-amino-5-(4- ...