Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron
作者:Zhongxing Zhang、Zhiwei Yin、Nicholas A. Meanwell、John F. Kadow、Tao Wang
DOI:10.1021/ol0300773
日期:2003.9.1
[reaction: see text] Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.
Imidazole-Catalyzed Monoacylation of Symmetrical Diamines
作者:Sanjeev K. Verma、B. N. Acharya、M. P. Kaushik
DOI:10.1021/ol101604q
日期:2010.10.1
An imidazole-catalyzed protocol for monoacylation of symmetricaldiamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.