Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions

TETRAHEDRON LETTERS

卷:56

Article

Hoshino, Yujiro¹  Shimbo, Yuki¹  Ohtsuka, Naoya¹  Honda, Kiyoshi¹ 

[1] Yokohama Natl Univ, Grad Sch Environm & Informat Sci, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

关键词: Lossen rearrangement;    Hydroxamic acids;    Amines;    Activating agents;   

DOI  :  10.1016/j.tetlet.2014.12.084

来源: Elsevier

【 摘 要 】

A mild self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields. This alternative to traditional Lossen rearrangement provides a simple and mild method for the synthesis of amines from free hydroxamic acids. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free