143283-95-8Relevant articles and documents
Cyanide-Catalyzed Cyclizations via Aldimine Coupling
Reich, B. Jesse E.,Justice, Aaron K.,Beckstead, Brittany T.,Reibenspies, Joseph H.,Miller, Stephen A.
, p. 1357 - 1359 (2007/10/03)
Aldimine coupling (AIC) is the nitrogen analogue of the benzoin condensation and has been applied to dialdimines, providing the first examples of cyclizations effected by cyanide-catalyzed AIC. Sodium cyanide promoted the facile, intramolecular cyclization of several dialdimines in N,N-dimethylformamide, methanol, or methylene chloride/water (phase-transfer conditions) yielding a variety of six-membered heterocycles. Under aerobic conditions, an oxidative cyclization occurs to provide the diimine heterocycle. Oligomerization was observed with rigid dialdimines for which cyclization was precluded.