Journal
HETEROCYCLES
Volume 77, Issue 1, Pages 263-272Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-08-S(F)4
Keywords
5-Methoxycarbonyl-1-sulfonylpyridone; 2-Sulfonyl-1-isoquinolone; 5,4-Dimethoxycarbonyl-1-sulfonylpyridone; Diels-Alder Reaction; MO Calculation
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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.
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