Cycloaddition of 2(1H)-Pyridones Having a Methoxycarbonyl Group to 1, 3-Butadiene Derivatives

Reiko FUJITA; Masato HOSHINO; Hiroshi TOMISAWA; Hisao MATSUZAKI; Hiroshi HONGO

doi:10.1248/cpb.49.497

Notes

Cycloaddition of 2(1H)-Pyridones Having a Methoxycarbonyl Group to 1, 3-Butadiene Derivatives

Reiko FUJITA, Masato HOSHINO, Hiroshi TOMISAWA, Hisao MATSUZAKI, Hiroshi HONGO

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Keywords: 6-methoxycarbonyl-2(1H)-pyridone, phenanthridone, isoquinolone, electron-withdrawing group, cycloaddition, Gaussian 98

JOURNAL FREE ACCESS

2001 Volume 49 Issue 4 Pages 497-500

DOI https://doi.org/10.1248/cpb.49.497

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Abstract

The cycloaddition of 4-methoxycarbonyl-2(1H)-pyridones to silyloxydienes gave isoquinolone derivatives in reasonable yields. Furthermore, the cycloaddition of 6-methoxycarbonyl-2(1H)-pyridones to 2, 3-dimethyl-1, 3-butadiene produced cycloadducts (isoquinolone and quinolone derivatives) and double cycloadducts (phenanthridone derivatives). The activation energies using Gaussian 98 with RHF/3-21G level of 4- and 6-methoxycarbonyl-2(1H)-pyridones coincided with the experimental facts.

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