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Molecules 2012, 17(6), 6519-6546; doi:10.3390/molecules17066519
Article

Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds

1,* , 1, 1, 1, 1, 1,†, 1,‡, 2,# and 1,§,*
1 Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan 2 Graduate School of Engineering, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan Current Address: Laboratory of Molecular Biochemistry, Department of Biomolecular Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. Current Address: 6 Haruna-cho, Tanaka-nishi, Sakyou-ku, Kyoto 606-8235, Japan. # Current Address: 1-22, Minami 7-jo, Nishi 16-chome, Chuo-ku, Sapporo 064-0807, Japan. § Current Address: School of Pharmacy, Aichi Gakuin University, 1-100 Kusumoto-cho, Nagoya 464-8650, Japan.
* Authors to whom correspondence should be addressed.
Received: 28 April 2012 / Revised: 21 May 2012 / Accepted: 21 May 2012 / Published: 30 May 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
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Abstract

The reaction of 5-halogenouracil and uridine derivatives 1 and 7 with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as the regioselective C-C bond formation at the 5- and 6-positions of uracil and uridine derivatives (products 2, 5, 8, 17, 20 and 21), and the formation of fused heterocycle derivatives 2,4-diazabicyclo[4.1.0]heptane (15) and 2,4-diazabicyclo-[4.1.0]nonane (16) via dual C-C bond formations at both the 5- and 6-positions were due to the different active methylene compounds used as reagents.
Keywords: C-C bond formation; active methylene; carbanion; uracil; uridine C-C bond formation; active methylene; carbanion; uracil; uridine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Sajiki, H.; Iida, Y.; Ikawa, K.; Sawama, Y.; Monguchi, Y.; Kitade, Y.; Maki, Y.; Inoue, H.; Hirota, K. Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds. Molecules 2012, 17, 6519-6546.

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