Synthesis of highly functionalized strained bicyclic dilactam derivatives

ABSTRACT

An efficient and modest protocol has been utilized for the synthesis of bicyclic dilactam derivatives through one-pot multicomponent domino reaction starting from various cyclic ketones under mild condition. The synthesized motif shows four stereogenic centers with two quaternary amine functionalities and such molecular arrangements are very fascinating and rare to obtain. We propose a mechanism for the formation of bicyclic dilactams through aldol condensation/condensation of cyanoacetamides/cyclization of condensed intermediate.

GRAPHICAL ABSTRACT

KEYWORDS:

• Bicyclic dilactams
• domino reaction
• four component
• multicomponent reactions
• quinoline

Additional information

Funding

The DST-FIST NMR facility at VIT University is greatly acknowledged. The authors gratefully acknowledge VIT University, Vellore for the support through Seed Grant for Research. G. Ramachandran would like to thank JSPS for the postdoctoral fellowship (Grant Number: JP16F16339).