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

Molecules

Hironao Sajiki¹  Yusuke Iida¹  Kanoko Ikawa¹  Yoshinari Sawama¹  Yasunari Monguchi¹  Yukio Kitade¹  Yoshifumi Maki¹  Hideo Inoue¹ 

[1] ¹Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

关键词: C-C bond formation;    active methylene;    carbanion;    uracil;    uridine;   

DOI  :  10.3390/molecules17066519

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
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