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Communication | Special issue | Vol 35, No. 1, 1993, pp.89-92
Published online, 1st January, 1970
DOI: 10.3987/COM-92-S33
Sequential C-2 Lithiation/Acylation of N-1 Functionalized Imidazoles: Synthesis of Novel Tetrahydroimidazo[1,2-a][1,4]diazepines

William J. Hoekstra* and Jeffery B. Press

*The R. W. Johnson Pharmaceutical Research Institute, Spring House, PA 19477, U.S.A.


5,6,7,9-Tetrahydroimidazo[1,2-a][1,4]diazepines (4a-c) are prepared by conversion of 2-acylimidazoles (2a-c) to cyclic imines (3a-c) followed by hydride reduction. In the key step, a masked primary amine (1) is acylated in good yield employing an alkyllithium base to afford acylimidazoles (2a-c) after acid hydrolysis of the imines. This reaction avoids use of transient N-1 (im) protecting groups.