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Paper | Special issue | Vol 77, No. 1, 2009, pp.263-272
Published online, 14th March, 2008
DOI: 10.3987/COM-08-S(F)4
Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen

Masato Hoshino, Kazuhiro Watanabe, Yosuke Ohtake, Takeshi Sato, Hisao Matsuzaki, and Reiko Fujita*

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Diels-Alder (DA) reaction of 5-methoxycarbonyl-2-pyridone, which has an electron-withdrawing acyl group at nitrogen, with 1,3-diene afforded 2-quinolone derivatives in modest yields. Further, DA reaction of 5,4-dimethoxycarbonyl-1-sulfonyl-2-pyridone gave 2-quinolone and 1-isoquinolone (1:1). DA reaction of 2-sulfonyl-1-isoquinolone afforded a functionalized phenanthridone. The site-selectivity was well correlated with the corresponding activation energies calculated using an ab initio molecular orbital method.