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Synlett 2022; 33(03): 207-223
DOI: 10.1055/s-0040-1719830
DOI: 10.1055/s-0040-1719830
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Domino Reactions of Chromones with Heterocyclic Enamines
Dedicated to Dr. Jorge Jios on the occasion of his 60th 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
Publikationsverlauf
Eingereicht: 29. Juli 2021
Angenommen nach Revision: 11. August 2021
Artikel online veröffentlicht:
02. September 2021
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