Domino Reactions of Chromones with Heterocyclic Enamines

Dedicated to Dr. Jorge Jios on the occasion of his 60^th birthday

Abstract

Domino reactions of heterocyclic enamines with chromone derivatives provides a convenient synthesis of a great variety of annulated heterocyclic ring systems. The course of the reaction depends on the type of substituent located at position 3 of the chromone. Reactions of 3-unsubstituted chromones, 3-nitrochromones, and 3-halochromones proceed by conjugate addition of the carbon atom of the enamine to carbon C-2 of the chromone, ring cleavage, and recyclization via the chromone carbonyl group. In the case of 3-formylchromes, 3-dichloroacetylchromone, 3-perfluoroalkanoylthiochromones, 3-(2-fluorobenzoyl)chromones, and 3-methoxalylchromones the final cyclization proceeds via the carbonyl group located outside the chromone moiety. The functional groups located at the carbonyl group at position 3 of the chromone allow for further synthetic transformations including additional ring closures.

Contents

1 Introduction

2 3-Unsubstituted Chromones

3 3-Nitrochromones

4 3-Formylchromes

5 3-Dichloroacetylchromone

6 3-Perfluoroalkanoylthiochromones

7 3-Methoxalylchromones

8 3-(2-Fluorobenzoyl)chromones

9 3-Halochromones

10 Chromone-3-carboxylic Acids

11 Conclusions

Key words

chromones - enamines - domino reactions - cyclization - heterocycles

Publication History

Received: 29 July 2021

Accepted after revision: 11 August 2021

Article published online:
02 September 2021

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