94559-36-1Relevant articles and documents
Reactions with Aziridines, 30. - Synthesis of 2-(Acylimino)pyrrolidines and N-Acylated γ-Aminobutyronitriles by Amidoethylation of Simple Nitriles with N-Acylaziridines
Woderer, Anton,Assithianakis, Petros,Wiesert, Wolfgang,Speth, Dieter,Stamm, Helmut
, p. 3348 - 3364 (2007/10/02)
Mono- and disubstituted acetonitriles 3a-j in their deprotonated form are amidoethylated at the α-carbon with the N-acylaziridines 5a-d under aprotic conditions.The anionic primary products 6 and 20e, i may undergo a second amidoethylation if derived from a mono-substituted acetonitrile, and they may cyclize followed by migration of the acyl group.Thus, the N-acylated α-substituted γ-aminobutyronitriles 7b-g, i-o, the N,N'-diacylated 1,5-diamino-3-cyanopentanes 15d, f, g and 22e, i, the 2-(acylimino)pyrrolidines 10a-c, e, f, h-j, and the 3-amidoethylated2-(acylimino)pyrrolidines 16e, f, h, i are obtained.Once, 6 was a second time amidoethylated at the amide nitrogen.In one case, the 3-cyano-2-pyrrolidone 25 was formed by amidoethylation, elimination of Ph2N-, and cyclization of the intermediated isocyanate.The cyclization may be prevented by using lithium as gegenion or by using a protic solvent.Base catalyzed solvolysis of an (acylimino)pyrrolidine removes the acyl group if this is ethoxycarbonyl and cleaves the C=N double bond if the acyl group is benzoyl.
