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Communication | Special issue | Vol 8, No. 1, 1977, pp.165-170
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0165
Reaction of 1-Methyl-2(1H)-pyridone with Fumaric Acid and Its Ester

Hiroshi Tomisawa,* Hiroshi Hongo, Reiko Fujita, Hideki Kato, and Akira Sato

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

Abstract

The further studies on the Diels-Alder reaction of 1-methyl-2(1H)-pyridone (I) with fumaric acid and its ester were carried out in various conditiocs. Reaction of I with dimethyl fumarate in toluene gave dimethyl 2- methyl-3-oxo-2-azabicycl[2,2,2]oct-7-ene-5-endo-6-exodicarboxylate (IV). Boiling of I and fumaric acid in water afforded 6-methyl-7-oxo-6-azabicycl[3,2,1]oct-2-ene-2,8-endo-dicasboxylic acid (VI). Heating of I and fumaric acid at 170° gave VI and 6-methyl-7-oxo-6-azabicyclo[3,2,1]oct-2-ene-2,8-exo-dicarboxylic acid (VII).