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A new ring-opening reaction of 5,6-dihydro-2-pyridones was discovered. Compounds 1 and 7 were converted to the dienoic amides 2 and 8 by reaction with sodium hydride at room temperature. N-Allylation of compounds 2 and 8 followed by IMDA reaction provided the cis-fused hexahydro-1-indolones 5 and 10, respectively. Treatment of compounds 5 and 10 with DBU in refluxing ethyl acetate gave the conjugated...
Cycloaddition reactions of sulfoxide- and sulfone-substituted dihydro-2-pyridones and 2-pyridones with electron-rich dienes gave new bicyclic and tricyclic products in good to fair yields. The reactivity, regioselectivity, and stereoselectivity of these reactions were compared with semi-empirical theoretical calculations. Evidence is provided for rather unusual two parallel reaction pathways for the...
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