336854-86-5Relevant articles and documents
Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles
Zhang, Lidan,Xiao, Ke,Qiao, Yan,Li, Xin,Song, Chuanjun,Chang, Junbiao
supporting information, p. 6913 - 6918 (2018/12/05)
Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.
SnCl2-catalyzed propargylic substitution of propargylic alcohols with carbon and nitrogen nucleophiles
Masuyama, Yoshiro,Hayashi, Miki,Suzuki, Noriyuki
, p. 2914 - 2921 (2013/07/05)
A weak Lewis acid, tin(II) chloride, which is insensitive to water and air, functioned as a catalyst for the propargylic substitution of secondary propargylic alcohols with carbon nucleophiles, such as electron-rich arenes, heteroarenes, and 1,3-dicarbony
Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides
Zhang, Xiaoxiang,Teo, Wan Teng,Chan, Philip Wai Hong
experimental part, p. 331 - 337 (2011/02/17)
An efficient synthetic method to prepare di- and trisubstituted 2-aryloxazoles based on Yb(OTf)3 catalyzed cyclization of trisubstituted propargylic alcohols with aryl amides is described. The reaction was accomplished in moderate to excellent product yields and with complete regioselective control. The mechanism is suggested to involve activation of the starting alcohol by the metal catalyst that results in its ionization. Subsequent cyclization of this newly generated carbocationic species with the aryl amide then affords the oxazole. In view of the mild conditions along with the low cost, commercially availability of Yb(OTf)3 and its high tolerance to air and moisture, the present synthetic approach offers an operationally simplistic and convenient route to this important aromatic heterocycle.