120230-90-2Relevant academic research and scientific papers
Microwave-assisted sequential amide bond formation and intramolecular amidation: A rapid entry to functionalized oxindoles
Poondra, Rajamohan R.,Turner, Nicholas J.
, p. 863 - 866 (2005)
(Chemical Equation Presented) A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
supporting information, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts
Sallio, Romain,Payard, Pierre-Adrien,Pakulski, Pawe?,Diachenko, Iryna,Fabre, Indira,Berteina-Raboin, Sabine,Colas, Cyril,Ciofini, Ilaria,Grimaud, Laurence,Gillaizeau, Isabelle
, p. 15885 - 15889 (2021/05/19)
This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.
BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles
Xu, Chuangchuang,Xu, Jiaxi
, p. 127 - 134 (2019/12/26)
Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.
Copper-catalyzed aerobic oxidative annulation and carbon-carbon bond cleavage of arylacetamides: Domino synthesis of fused quinazolinones
Sun, Jie,Tan, Qitao,Yang, Wusong,Liu, Bingxin,Xu, Bin
supporting information, p. 388 - 394 (2014/05/20)
An efficient copper-catalyzed tandem aerobic oxidative annulation and carbon-carbon bond cleavage reaction was developed from easily accessible arylacetamides, which provides a direct approach for the domino synthesis of a vast array of tricyclic or tetracyclic fused quinazolinone alkaloid structures. A plausible reaction mechanism is proposed involving an aerobic benzylic oxidation/ cyclization/decarbonylation cascade.
