A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
(1999) Tetrahedron — Vol. 55, n° 11, p. 3387-3400 (1999)
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- :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.
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Ghosez, L., Jnoff, E., Bayard, P., Sainte, F., & Beaudegnies, R. (1999). A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy. Tetrahedron, 55(11), 3387-3400. https://doi.org/10.1016/S0040-4020(98)01149-1 (Original work published 1999)