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Note | Regular issue | Vol 55, No. 10, 2001, pp.1971-1980
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9306
Quinoline Ring Formation by Cycloaddition of N-Arylketenimines with Enol Ethers under High Pressure

Masao Shimizu,* Akihiro Oishi, Yoichi Taguchi, Tomohumi Sano, Yasuo Gama, and Isao Shibuya

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan

Abstract

The reaction of N-aryl substituted ketenimines with enol ethers under 800 MPa gave quinoline derivatives, which formed by cyclization between the C=C-N=C aza-diene moieties of N-aryl substituted ketenimines and the C=C double bond moieties of enol ethers. When cyclic enol ethers such as 2,3-dihydrofurans or 3,4-dihydro-2H-pyrans were used as dienophiles, quinoline derivatives that had substituents with hydroxyalkyl or oxoalkyl side chains on the C-3 positions were synthesized in one step reaction.