584-70-3Relevant articles and documents
Derivatives from isoselenocyanates: Synthesis of 2-phenyl-6H-[5,1,3] benzoselenadiazocine
Atanassov, Plamen K.,Linden, Anthony,Heimgartner, Heinz
, p. 1452 - 1466 (2004)
The reaction of N-phenylbenzimidoyl isoselenocyanates 8 with primary and secondary amines in acetone at room temperature, followed by treatment with a base, led to 6H-[5,1,3]benzoselenadiazocine derivatives of type 10 (Scheme 3). An analogous cyclization was observed when 8a and 8b were reacted with the Na salt of diethyl malonate in EtOH at room temperature, which yielded the eight-membered selenaheterocycles 11 (Scheme 5). The molecular structures of some of the products, as well as that of a sulfur analogue, have been established by X-ray crystallography (Figs. 1-4). The isoselenocyanates 8 have been prepared from N-(2-methylphenyl)benzamides 5 in a three-step procedure via the corresponding imidoyl chlorides 6, side-chain chlorination to give 7, and treatment with KSeCN (Scheme 2).
Iron-catalyzed oxidative amidation of acylhydrazines with amines
Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
supporting information, (2021/08/18)
A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
Manganese Catalyzed Direct Amidation of Esters with Amines
Fu, Zhengqiang,Wang, Xinghua,Tao, Sheng,Bu, Qingqing,Wei, Donghui,Liu, Ning
, p. 2339 - 2358 (2021/02/03)
The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.