Multicomponent Reactions with Cyclic Tertiary Amines Enabled by Facile C−N Bond Cleavage

Abstract

An ovel and catalyst-free multicomponent reaction with cyclic tertiary amines,e lectron-deficient aryl halides or heteroaromatic halides,and Na 2 Senabled by facile CÀNbond cleavage of the cyclic tertiary amines was developed. This direct and operationally simple method can be applied with awide range of functional groups and provides an efficient and rapid approacht op otentially drug-like products containing amine,a zaarene,t hioether,o rp henol ether functionalities in good to excellent yields.T he utility of this method was demonstrated by the rapid synthesis of the analgesic ruzadolane.Scheme 1. An ew multicomponent reaction via CÀNbond cleavage.

Synthesis of N‐alkyl‐N′‐aryl or Alkenylpiperazines: A Copper‐Catalyzed C–N Cross‐Coupling in the Presence of Aryl and Alkenyl Triflates and DABCO

“…These studies are very well recapitulated in a review written by Dai . Since the pioneering work of Ross and Finkelstein , the ring‐opening of DABCO prompted by nucleophilic attack on the corresponding bicyclic quaternary ammonium salts have been well developed over the past decades . The literature on ring‐opening reactions of quinuclidine derivatives has been reviewed up to the year 1984 .…”