Convenient Route to 2H-Pyrrolo[3,4-b]quinolin-9(4H)-one Skeleton via TosMIC Reaction

Abstract

A practical and versatile method for the synthesis of 2H-pyrrolo[3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.

GRAPHICAL ABSTRACT

Keywords:

• Heteroaromatic
• microwave
• quinoline
• TosMIC

ACKNOWLEDGMENT

The authors thanks Italian MIUR for financial support under PRIN 2008 (2008CE75SA).

Notes

^a Ratios are referred to 1 eq of quinolinone 1d.