4.4 Article

An Efficient Strategy for the Synthesis of 1,6-Naphthyridine-2,5-dione Derivatives under Ultrasound Irradiation

Journal

SYNLETT
Volume 31, Issue 13, Pages 1313-1317

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707469

Keywords

aminopyridinones; naphthyridines; green chemistry; sonochemistry; multicomponent reaction; domino reaction

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A flexible and efficient three-component reaction has been established for the synthesis of bioactive 1,6-naphthyridine-2,5-diones by using low-cost and readily accessible aminopyridinones, aromatic aldehydes, and Meldrum's acid as starting materials. The main advantage of this synthetic method is that the yields of the resulting 1,6-naphthyridine-2,5-dione derivatives under ultrasound irradiation in water with acetic acid as catalyst are higher than those from the classical-heating method. The probable reaction mechanism indicates that the process involves a Knoevenagel condensation, Michael addition, and cyclization sequence.

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