Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels-Alder reactions.

Beilstein J Org Chem

Institut de Chimie Organique & Analytique, Université d'Orléans, UMR-CNRS 7311, BP 6759, 45067 Orléans Cedex 2, France.

Published: March 2014

Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels-Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels-Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943289PMC
http://dx.doi.org/10.3762/bjoc.10.24DOI Listing

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