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Communication | Regular issue | Vol 9, No. 12, 1978, pp.1745-1748
Published online, 1st January, 1970
DOI: 10.3987/R-1978-12-1745
Selective N-Alkylation of Enaminone Anions Leading to 3-N-Aziridyl-, -Azetidyl-, and -Pyrrolidylcyclohex-2-en-1-ones

Hideo Iida,* Yoshifumi Yuasa, and Chihiro Kibayashi

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Double N-alkylation of 3-aminocyclohex-2-en-1-one (1) with 1,4-dibromobutane in the presence of sodium hydride gave 3-N-pyrroljdylcyclohex-2-en-1-one (6). The formation of the N-aziridyl and -azetidyL analogues (2 and 3) of 6 was achieved by internal N-alkylation of the N-ω-haloalkyl derivatives of 1 with appropriate strong bases.