53399-10-3Relevant academic research and scientific papers
Facile synthesis of 2-alkenylazaarenes via dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’
Fu, Shiheng,Wang, Liang,Dong, Haoxun,Yu, Junqiang,Xu, Lubin,Xiao, Jian
supporting information, p. 4533 - 4536 (2016/09/23)
A catalyst-free dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’ has been developed for efficient synthesis of (E)-2-alkenylazaarenes. The challenging addition/dehydration of aliphatic aldehyde was successfully implemented using water as a solvent. A variety of 2-methylazaarenes, aromatic and aliphatic aldehydes were well tolerated.
Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals
Shi, Shuai,Wang, Tao,Weingand, Vanessa,Rudolph, Matthias,Hashmi, A. Stephen K.
, p. 1148 - 1151 (2014/03/21)
The reaction of an α-ketoaldehyde and a terminal alkyne in the presence of piperidine and a catalytic amount of AuCl delivers 1,2-dicarbonyl-3-enes, products of the formal hydroacylation of the triple bond. The scope of the method is broad; different aryl substituents on the dicarbonyl unit and on the alkyne are well tolerated. The products can be transformed selectively into vinylquinoxalines. Mechanistic studies, including isotope-labeling experiments, indicate that after an initial A3-type conversion to propargylic amines, a subsequent base-mediated alkyne-to-allene isomerization and a hydrolysis of the enamine substructure during the workup deliver the formal hydroacylation products. The simple AuCl catalyst and piperidine convert terminal alkynes and α-ketoaldehydes into 1,2-dicarbonyl-3-enes, the products of a formal hydroacylation of the triple bond, with excellent regio- and diastereoselectivity. There is no evidence for classical A3 coupling products, which could be expected from such a gold-catalyzed reaction of an aldehyde, an amine, and a terminal alkyne. Copyright
