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Paper | Regular issue | Vol 51, No. 12, 1999, pp.2881-2892
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8688
CAN-mediated Formation of Furopyranones and Furoquinolinones

Kazuhiro Kobayashi,* Kouji Sakashita, Hideki Akamatsu, Koujirou Tanaka, Masaharu Uchida, Tomokazu Uneda, Taichi Kitamura, Osamu Morikawa, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

The reaction of 4-hydroxy-2H-pyran-2-one derivatives (1), (11), and (17) with a range of alkenes or phenylacetylene in acetonitrile containing cerium(IV) ammoniurn nitrate (CAN) afforded the corresponding furo[3,2-c]pyranone (4, 8, 13, 15, and 18) and/or furo[2,3-b]pyranone derivatives (6, 10, 14, 16, and 19). Similar treatment of 4-hydroxy-1-methylquinolin-2(1H)-one (2) with alkenes or phenylacetylene in the presence of CAN gave furo[3,2-c]quinolin-4(5H)-one derivatives (5) and (9).