Cyanomethylation and Cyclization of Aryl Alkynoates with Acetonitrile under Transition-Metal-Free Conditions: Synthesis of 3-Cyanomethylated Coumarins
Yu, YL (Yu, Yulan)[ 1 ] ; Zhuang, SY (Zhuang, Shengyi)[ 1 ] ; Liu, P (Liu, Ping)[ 1 ] ; Sun, PP (Sun, Peipei)[ 1 ]*
[ 1 ] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Jiangsu Prov Key Lab Mat Cycle Proc & Pollut Cont, Coll Chem & Mat Sci, Nanjing 210023, Jiangsu, Peoples R China
JOURNAL OF ORGANIC CHEMISTRY, Nov.2016, 81(22), 11489-11495
Cyanomethylated coumarins were synthesized via cyanomethylation and cyclization Of aryl alkynoates using cheap and available reagent acetonitrile as the cyanomethyl source in the presence of TBPB (tert-butyl peroxybenzoate) under transition-metal-free conditions. For the substrates with various substituents on benzene ring, the reaction proceeded smoothly to give the corresponding products in moderate to good yields. The resulting products could be simply converted into some other related coumarin derivatives.