A simple, convenient, and practical method for the synthesis of alpha-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected a-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported.
P. Galletti, M.Pori, D. Giacomini (2011). Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, -, 3896-3903 [10.1002/ejoc.201100089].
Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source
GALLETTI, PAOLA;PORI, MATTEO;GIACOMINI, DARIA
2011
Abstract
A simple, convenient, and practical method for the synthesis of alpha-amino nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected a-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2-diamines to obtain 1,2-diamino nitriles, and to cyclic secondary amines is reported.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
