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Paper | Regular issue | Vol 53, No. 5, 2000, pp.1021-1028
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8833
Convenient Direct Synthesis of Vinylogous Urea Derivatives Using Magnesium Amide-induced Amide/Nitrile Coupling

Kazuhiro Kobayashi,* Tomohide Kitamura, Ryoji Nakahashi, Akiko Shimizu, Keiichi Yoneda, Osamu Morikawa, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, Japan

Abstract

The magnesium enolates, generated by treatment of acyclic (1) and cyclic tertiary amides (4) with a (diisopropylamino)magnesium reagent, reacted efficiently with nitriles (2) to afford the corresponding β-aminoacrylamides (3) and α-(α-aminoalkylidene)lactams (5). The formation of α-(2-pyrrolidinylidene)lactams (7) from the reactions of N-methyl-2-pyrrolidone and N-methyl-2-piperidone with a γ-cyanopropyl p-toluenesulfonate (6) is also described.