1609958-86-2Relevant academic research and scientific papers
Synthesis of Sulfonamide-Based Ynamides and Ynamines in Water
Zhao, Lei,Yang, Hongyi,Li, Ruikun,Tao, Ye,Guo, Xiao-Feng,Anderson, Edward A.,Whiting, Andrew,Wu, Na
, p. 1938 - 1947 (2021/01/14)
Ynamides, though relatively more stable than ynamines, are still moisture-sensitive and prone to hydration especially under acidic and heating conditions. Here we report an environmentally benign, robust protocol to synthesize sulfonamide-based ynamides and arylynamines via Sonogashira coupling reactions in water, using a readily available quaternary ammonium salt as the surfactant.
A General Copper-Catalyzed Synthesis of Ynamides from 1,2-Dichloroenamides
Mansfield, Steven J.,Smith, Russell C.,Yong, Jonathan R. J.,Garry, Olivia L.,Anderson, Edward A.
, p. 2918 - 2922 (2019/04/25)
Ynamides are accessed via copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides. The reaction exhibits a broad substrate scope, is readily scaled, and overcomes typical limitations in ynamide synthesis such as the use of ureas, carbamates, and bulky or aromatic amide derivatives. This modular approach contrasts with previous routes by installing both the N- and C-substituents of the ynamide as nucleophilic components.
α-Imino Gold Carbenes from 1,2,4-Oxadiazoles: Atom-Economical Access to Fully Substituted 4-Aminoimidazoles
Zeng, Zhongyi,Jin, Hongming,Xie, Jin,Tian, Bing,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 1020 - 1023 (2017/03/15)
A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.
A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides
Santos, Micka?l Dos,Davies, Paul W.
supporting information, p. 6001 - 6004 (2014/05/20)
An efficient C-O, C-S and C-C bond-forming sequence leads to functionalised compounds bearing sulfur-substituted quaternary carbons. Ynamides are employed as diazo-equivalents to access the [2,3]-sigmatropic rearrangements of allyl sulfonium ylides by a t
