Efficient [5+1] Synthesis of 4-Quinolones by Domino Amination and Conjugate Addition Reactions of 1-(2-Fluorophenyl)prop-2-yn-1-ones with Amines

Abstract

A catalyst-free synthetic approach is described for the synthesis of 4-quinolone derivatives through a tandem amination/conjugated Michael addition sequence of 1-(2-fluorophenyl)prop-2-yn-1-one derivatives. The [5+1]-cyclization proceeds efficiently at a high temperature under an inert atmosphere with lithium carbonate as a base, and it provides a practical route to a diverse range of 4-quinolones. The mechanism was studied in details and several of the intermediates were isolated.

Key words

quinones - ketones - domino reactions - aminations - Michael­ additions - heterocycles

• References

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