Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate.
A novel approach to the synthesis of purines bearing functionalized carbon substituents or methyl in position 6 was developed. Under different reaction conditions, 6-halopurine derivatives could react with ethyl acetoacetate efficiently to yield 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates and 6-methylpurines respectively. No metal catalyst and ligand were required.
Qu
Gui-Rong
GR
College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, Henan, P. R. China.
Mao
Zhi-Jie
ZJ
Niu
Hong-Ying
HY
Wang
Dong-Chao
DC
Xia
Chao
C
Guo
Hai-Ming
HM
D000090:Acetoacetates / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry*
D000090:Acetoacetates; D004952:Esters; D006846:Hydrocarbons, Halogenated; D011687:Purines; C024840:ethyl acetoacetate