Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels-Alder reactions.
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.
['Fadel|Salah|S|', 'Hajbi|Youssef|Y|', 'Khouili|Mostafa|M|', 'Lazar|Said|S|', 'Suzenet|Franck|F|', 'Guillaumet|Gérald|G|']
1,2,4-triazine Sonogashira cross-coupling inverse-electron-demand Diels–Alder reaction microwave irradiation naphthyridin-2(1H)-ones