Substitutions of Lactones, Amides, Lactams and Imides

Conventional conversion of amide, lactam, imide, and urea carbonyl groups into enaminones, enamino esters, or enamino nitriles requires prior activation of the carbonyl groups either by alkylation to imino ethers, followed by reaction with activated methylene groups, or by thiation, e.g. with P2S5, to thiocarbonyl groups followed by alkylation (and possibly also oxidation), and, again, subsequent reac- 

Goschi, A. Eschenmoser, Helv. Chim. Acta 1971, 54, 710 W. Kantlehner, W. Kugel, H. Bredereck, Chem Ber. 1972, 105, 2264 W. Kantlehner, P. Eiascher, W. Kugel, E. Mohring, H. Bredereck, Liebigs Ann. Chem. 1978, 512 

Domsch, H. Eeger, U. Frick, A. Gotz, H.H. Hergott, K. Hofmann, W. Kober, K. Krageloh, T. Oesterle, W. Steppan, W. West, G. Simchen, Synthesis 1982, 

Desmoni, a.G. Invernezzi, A. Gamba, P. Quadrelli, P.P. Rhigetti, Gazz. Chim. Ital. 1991, 121, 483 

The bis(substituted) product 382 has previously been obtained in ca 53% yield via the bis-imino intermediate 383 on boiling succinodinitrile with ethyl sodiocya- 

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