TY - JOUR
T1 - A mild reduction of azomethines with zinc borohydride. Synthetic application to tandem alkylation-reduction of nitriles
AU - Kotsuki, Hiyoshizo
AU - Yoshimura, Naka
AU - Kadota, Isao
AU - Ushio, Yasuyuki
AU - Ochi, Masamitsu
N1 - Funding Information:
This work was partially supported by a Grant-in-Aid from the ministry of Education, Science and Culture, Japan (Grant No. 62540410).
Publisher Copyright:
© 1990 Georg Thieme Verlag. All rights reserved.
PY - 1990
Y1 - 1990
N2 - The reduction of Schiff bases; N-benzylidene- and N-(1-phenylethylidene)arylamines with zinc borohydride in diethyl ether gave the corresponding amines in excellent yield. Af-benzylidene-benzyl- and cyclohexylamine, N-(1-phenylethylidene)- and N-(cyclohexyl-idene)cyclohexylamines, however, require additional treatment with 6N HCl to liberate the amine-borane complex to give the corresponding amines in quanitative yield. The procedure was also applied in the tandem alkylation-reduction of nitriles to yield 1-phenylalkylamines in good yield.
AB - The reduction of Schiff bases; N-benzylidene- and N-(1-phenylethylidene)arylamines with zinc borohydride in diethyl ether gave the corresponding amines in excellent yield. Af-benzylidene-benzyl- and cyclohexylamine, N-(1-phenylethylidene)- and N-(cyclohexyl-idene)cyclohexylamines, however, require additional treatment with 6N HCl to liberate the amine-borane complex to give the corresponding amines in quanitative yield. The procedure was also applied in the tandem alkylation-reduction of nitriles to yield 1-phenylalkylamines in good yield.
UR - http://www.scopus.com/inward/record.url?scp=84985727413&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84985727413&partnerID=8YFLogxK
U2 - 10.1055/s-1990-26886
DO - 10.1055/s-1990-26886
M3 - Article
AN - SCOPUS:84985727413
SN - 0039-7881
VL - 1990
SP - 401
EP - 402
JO - Synthesis
JF - Synthesis
IS - 5
ER -