Tetrahedron

Highly regioselective and practical synthesis of 1-acyl-5-hydroxypyrazolines and 1-acyl pyrazoles from 1, 2-allenic ketones and hydrazides

S Guo, J Wang, D Guo, X Zhang, X Fan

Index: Guo, Shenghai; Wang, Jiliang; Guo, Dongqiang; Zhang, Xinying; Fan, Xuesen Tetrahedron, 2012 , vol. 68, # 38 p. 7768 - 7774

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Citation Number: 11

Abstract

A mild and highly regioselective synthesis of 1-acyl-5-hydroxypyrazolines has been achieved through the condensation of 1, 2-allenic ketones with hydrazides in the absence of any catalyst. Moreover, the obtained 1-acyl-5-hydroxypyrazolines can be easily transformed into 1-acyl pyrazoles under the promotion of BF3· Et2O. It was also found that 1-acyl pyrazoles can be produced directly from allenic ketones and hydrazides through a one- ...