Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.
Zhang, Yanmeng,Zhang, He,Gao, Ke
supporting information
p. 8282 - 8286
(2021/10/25)
Efficient synthesis of antihistamines clocinizine and chlorcyclizine
A simple and efficient route has been developed for the synthesis of anti-histamine drugs clocinizine and chlorcyclizine. The common intermediate 1-[(4-chloro phenyl) (phenyl)-methyl]-piperazine (8), is prepared from (4-chlorophenyl) (phenyl)-methanone (5), in three steps with excellent yields. All the reactions proceeded smoothly and the products were also isolated easily. Springer Science+Business Media, LLC 2011.
Venkat Narsaiah,Narsimha
p. 538 - 541
(2012/09/22)
Straightforward three-component synthesis of diarylmethylpiperazines and 1,2-diarylethylpiperazines
Several functionalized diarylmethylpiperazines and 1,2-diarylethylpiperazines have been synthesized in moderate to high yield according to a one-step three-component coupling between an aromatic or a benzylic organozinc reagent, a piperazine derivative, and an aromatic aldehyde. The procedure can be extended to the synthesis of benzylpiperazine derivatives or β-arylethylpiperazines toward the use of paraformaldehyde or aliphatic aldehydes.