107776-92-1Relevant academic research and scientific papers
Metal-free aminothiation of alkynes: Three-component tandem annulation toward indolizine thiones from 2-alkylpyridines, ynals, and elemental sulfur
Chen, Zhengwang,Liang, Pei,Xu, Fan,Deng, Zhen,Long, Lipeng,Luo, Guotian,Ye, Min
, p. 12639 - 12647 (2019)
A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.
Stereodivergent Allylation of Azaaryl Acetamides and Acetates by Synergistic Iridium and Copper Catalysis
Jiang, Xingyu,Boehm, Philip,Hartwig, John F.
supporting information, p. 1239 - 1242 (2018/02/09)
We report stereodivergent allylic substitution reactions of allylic esters with prochiral enolates derived from azaaryl acetamides and acetates to form products from addition of the enolates at the most substituted carbon of an allyl moiety with two catalysts, a chiral metallacyclic iridium complex and a chiral bisphosphine-ligated copper(I) complex, which individually control the configuration of the electrophilic and nucleophilic carbon atoms, respectively. By simple permutations of enantiomers of the two catalysts, all four stereoisomers of products containing two stereogenic centers were synthesized individually with high diastereoselectivity and enantioselectivity. A variety of azaaryl acetamides and acetates bearing pyridyl, benzothiazolyl, benzoxazolyl, pyrazinyl, quinolinyl and isoquinolinyl moieties were all found to be suitable for this transformation.
Catalytic amidation of unactivated ester derivatives mediated by trifluoroethanol
Caldwell, Nicola,Jamieson, Craig,Simpson, Iain,Watson, Allan J. B.
supporting information, p. 9495 - 9498 (2015/06/08)
A catalytic amidation method has been developed, employing 2,2,2-trifluoroethanol to facilitate condensation of unactivated esters and amines, enabling the synthesis of a range of amide products in good to excellent yields. Mechanistic studies indicate the reaction proceeds through a trifluoroethanol-derived active ester intermediate.
Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
Baruah, Pranjal K.,Dinsmore, Jason,King, Amber M.,Salomé, Christophe,De Ryck, Marc,Kaminski, Rafal,Provins, Laurent,Kohn, Harold
, p. 3551 - 3564 (2012/07/28)
N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.
