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

Hironao Sajiki 1,* email, Yusuke Iida 1 , Kanoko Ikawa 1 , Yoshinari Sawama 1 , Yasunari Monguchi 1 , Yukio Kitade 1,† , Yoshifumi Maki 1,‡ , Hideo Inoue 2,#  and Kosaku Hirota 1,§,* email
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; in revised form: 21 May 2012 / Accepted: 21 May 2012 / Published: 30 May 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
PDF Full-text Download PDF Full-Text [491 KB, uploaded 30 May 2012 09:50 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

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.

AMA Style

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(6):6519-6546.

Chicago/Turabian Style

Sajiki, Hironao; Iida, Yusuke; Ikawa, Kanoko; Sawama, Yoshinari; Monguchi, Yasunari; Kitade, Yukio; Maki, Yoshifumi; Inoue, Hideo; Hirota, Kosaku. 2012. "Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds." Molecules 17, no. 6: 6519-6546.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert