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Communication | Regular issue | Vol 14, No. 6, 1980, pp.809-812
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0809
Reaction of Quinoline Methiodide with Bromo- or p-Toluenesulfonyloxy-acetonitrile Derivatives. Formation of a Novel Tricyclic Diazanonane System

Seitaro Saeki,* Yoshio Kaku, Masatomo Hamana,* and Hiroshi Noda

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

Quinoline methiodide (1) reacts with ethyl bromocyanoacetate (2a) in the presence of triethylamine to afford ethyl 2-methyl-9-oxo-2,10-diazabenzo[c]tricyclo[4,2,1,07,11]nonane-8-carboxylate (3a) in 24.1% yield. The products of the same type (3b-d and 3f) are obtained from reactions of 1 with bromocyanoacetamide (2b), α-bromophenylacetonitrile (2c), α-bromo-p-nitrophenylacetonitrile (2d), and o-tosylates of benzaldehyde and p-chlorobenzaldehyde cyanohydrins (2e and 2f).