Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate in the smiles rearrangement reaction: straightforward synthesis of amino acid derived quinolin-2(1H)-one enamines

This paper describes the development of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate compound as a heterocyclic enols containing a Michael acceptor so that it participates in an Ugi-type multicomponent condensation through a Smiles rearrangement in replacement of acid components. The new four-component containing 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, aldehyde derivatives, amine derivatives and isocyanides process leads readily and efficiently to heterocyclic enamines. This report is an outstanding strategy for the preparation of new biologically structures containing peptidic or pseudo-peptidic with quinolin-2(1H)-one scaffolds.

Automated summary

This paper describes the development of a compound called 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, which acts as a heterocyclic enol containing a Michael acceptor and participates in a multicomponent condensation through a Smiles rearrangement. The four-component reaction involving this compound, aldehyde derivatives, amine derivatives, and isocyanides leads to the formation of heterocyclic enamines in a facile and efficient manner. This study presents an excellent strategy for synthesizing new biologically active compounds with quinolin-2(1H)-one scaffolds.