1005500-94-6Relevant articles and documents
Direct Hydroheteroarylation of Ynamides with 2H-Tetrazoles: Regio- and Stereoselective Synthesis of (Z)-α-Tetrazole Enamides
Zhu, Jiekun,Wang, Qingbo,Meng, Xin,Zhao, Changyin,Sun, Xuejun,Tian, Laijin,Cao, Ziping
, p. 4066 - 4070 (2019)
We herein report the direct reaction of ynamides with 2H-tetrazoles under metal-free conditions to provide a variety of functionalized (Z)-α-tetrazole enamide products in high yields, including the N-2 and N-1 adducts that are easily separated. The reacti
Synthesis of poly-functionalized benzofurans: Via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides
Zhang, Dongxin,Man, Jingjing,Chen, Yan,Yin, Lei,Zhong, Junchao,Zhang, Qian-Feng
, p. 12567 - 12571 (2019)
Densely substituted amino-functionalized benzofurans were concisely accessed via the first one-pot domino oxidation/[3+2] cyclization of a hydroquinone ester and easily accessible ynamides under mild conditions in a short time. The complex benzofurans wer
Reactivity of ynamides with AlCl3 and ICl: Ready access to (E)-α-chloroenamides and (E/Z)-α-chloro-β-iodo-enamides
Siva Reddy, Alla,Anitha, Mandala,Suraj,Kumara Swamy
, (2021)
Abstract: AlCl3 acts as a chlorinating agent for ynamides in the presence of stoichiometric amount of water in the environmentally benign solvent dimethylcarbonate, affording efficient access to (E)-α-chloroenamides via hydrochlorination, with water as a protic source. The role of water in the reaction was proven by deuterium labelling experiment. Epoxy-ynamides undergo iodochlorination in addition to the cleavage of the epoxy ring to afford (E/Z)-α-chloro-β-iodo-enamides. Regio- and stereochemical assignments for the products are based on X-ray crystallographic studies. Graphic abstract: Chloroenamides are formed regio- and stereo-specifically via hydrochlorination of ynamides with AlCl3+H2O (1:1) in a dimethyl carbonate; aryl substituted epoxy ynamides afford (iodo)(chloro) enamides upon treatment with ICl.[Figure not available: see fulltext.]
Direct oxidation ofN-ynylsulfonamides intoN-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant
Dong, Jun,Fu, Duo,Sheng, Dongning,Wang, Jiayi,Xu, Jiaxi
, p. 40243 - 40252 (2021/12/31)
N-Arylethynylsulfonamides are oxidized intoN-sulfonyl-2-aryloxoacetamides directly and efficiently with dimethyl sulfoxide (DMSO) as both an oxidant and solvent with microwave assistance. DFT calculations indicate that DMSO nucleophilically attacks the ethylic triple bond and transfers its oxygen atom to the triple bond to form zwitterionic anionicN-sulfonyliminiums to trigger the reaction. Then it nucleophilically attacks the generated iminium intermediates to accomplish the oxidationviathe second oxygen atom transfer. The current method provides a straightforward and efficient strategy to transform variousN-arylethynylsulfonamides intoN-sulfonyl-2-aryloxoacetamides, sulfonyl oxoacetimides, without any other electrophilic activators or oxidants.
Facile one-pot synthesis of 2-aminoindoles from simple anilines and ynamides
Kim, Young Ho,Yoo, Huen Ji,Youn, So Won
supporting information, p. 13963 - 13966 (2020/11/20)
A highly effective and straightforward one-pot synthesis of diversely substituted 2-aminoindoles has been developed, involving sequential Au(i)-catalyzed regioselective hydroamination and CuCl2-mediated oxidative cyclization. This protocol offers an operationally easy, simple, robust, and sustainable approach with the use of readily available starting materials, good functional group tolerance, and high practicality and efficiency. This journal is
