Stereoselective Synthesis of Tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones from 5-Fluoro-1,3-dimethyluracil and Naphthalenes

Kazue Ohkura; Tetsuya Ishihara; Ken-ichi Nishijima; James Michael Diakur; Koh-ichi Seki

doi:10.1248/cpb.53.258

Communications to the Editor

Stereoselective Synthesis of Tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones from 5-Fluoro-1,3-dimethyluracil and Naphthalenes

Kazue Ohkura, Tetsuya Ishihara, Ken-ichi Nishijima, James Michael Diakur, Koh-ichi Seki

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Keywords: stereoselective synsthesis, 1,2-photocycloaddition, 5-fluoro-1,3-dimethyluracil, naphthocyclobutapyrimidine, piperylene

JOURNAL FREE ACCESS

2005 Volume 53 Issue 2 Pages 258-259

DOI https://doi.org/10.1248/cpb.53.258

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Abstract

Upon UV-irradiation in the presence of piperylene, 5-fluoro-1,3-dimethyluracil (5-FDMU) couples with naphthalenes having either an electron-withdrawing group or an electron-donating group by way of 1,2-cycloaddition via mode selectivity to give the corresponding naphthocyclobutapyrimidines regio- and stereo-selectively.

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