Abstract
1-Alkyl-2-pyridones react with N-phenylmaleinimide and maleinimide stereoselectively via the scheme of the diene synthesis to give imides of 8-alkyl-8-azabicyclo[2.2.2]-4-octen-7-one-1,2-dioic acid. 3-Unsubstituted 2-pyridones form adducts with an endo configuration, whereas 1,3-dimethyl-2-pyridone gives an exo adduct under the same conditions. The endo- and exo-bridge adducts readily undergo retrograde diene disintegration on heating.
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See [1] for communication XIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1512–1515, November, 1974.
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Shusherina, N.P., Betaneli, L.V., Mndlyan, G.B. et al. Diene synthesis with 2-pyrones and 2-pyridones XIV. 1,4-Cycloadducts of 1-alkyl-2-pyridones with N-phenylmaleinimide and maleinimide. Chem Heterocycl Compd 10, 1329–1331 (1974). https://doi.org/10.1007/BF01175091
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DOI: https://doi.org/10.1007/BF01175091