99839-93-7Relevant academic research and scientific papers
Electrochemical Synthesis of Cyanoformamides from Trichloroacetonitrile and Secondary Amines Mediated by the B12Derivative
Moniruzzaman, Mohammad,Yano, Yoshio,Ono, Toshikazu,Shimakoshi, Hisashi,Shiota, Yoshihito,Yoshizawa, Kazunari,Hisaeda, Yoshio
, p. 16134 - 16143 (2021/07/19)
The B12derivative, heptamethyl cobyrinate, -mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiatedin situgeneration of the reactive acyl chloride intermediate, whic
The synthesis of cyanoformamides via a CsF-promoted decyanation/oxidation cascade of 2-dialkylamino-malononitriles
Lei, Lin-Sheng,Xue, Cao-Gen,Xu, Xue-Tao,Jin, Da-Ping,Wang, Shao-Hua,Bao, Wen,Liang, Huan,Zhang, Kun,Asiri, Abdullah M.
, p. 3723 - 3726 (2019/04/17)
A mild and efficient method for the synthesis of cyanoformamides from N,N-disubstituted aminomalononitriles with CsF as the promoter has been developed. This method features a wide substrate scope and high reaction efficiency, and will facilitate corresponding cyanoformamide-based biological studies and synthetic methodology development.
Solvent-Free Synthesis of Cyanoformamides from Carbamoyl Imidazoles
Nugent, Jeremy,Campbell, Sarah G.,Vo, Yen,Schwartz, Brett D.
, p. 5110 - 5118 (2017/09/23)
A straightforward and solvent-free synthesis of various secondary and tertiary cyanoformamides from carbamoyl imidazoles and TMSCN has been developed. Both cyclic and acyclic carbamoyl imidazoles react smoothly to form the relevant cyanoformamides in excellent yields, often within minutes.
Transition-Metal-Free Conversion of Trifluoropropanamides into Cyanoformamides through C-CF3 Bond Cleavage and Nitrogenation
Wang, Fang,Zhang, Tao,Tu, Hai-Yong,Zhang, Xing-Guo
, p. 5475 - 5480 (2017/05/24)
A new transition-metal-free transformation of trifluoropropanamides into cyanoformamides through a sequence of C-CF3 bond cleavage and nitrogenation using tert-butyl nitrite as the nitrogen source is described. The method features direct detrifluoromethylation, broad substrate scopes, and excellent selectivity control, representing a new shortcut for constructing the nitrile group involving C-CF3 σ-bond cleavage.
Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds
Kumar, Nivesh,Ghosh, Santanu,Bhunia, Subhajit,Bisai, Alakesh
supporting information, p. 1153 - 1169 (2016/07/06)
The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.
PhI(OAc)2-promoted metal-free oxidation of 2-oxoaldehydes: a facile one-pot synthesis of cyanoformamides
Zhan, Zhen,Cheng, Xu,Zheng, Yang,Ma, Xiaojun,Wang, Xiaoyu,Hai, Li,Wu, Yong
, p. 82800 - 82803 (2015/10/19)
A novel, efficient and environmental method for the conversion of 2-oxoaldehydes into cyanoformamides with iodosobenzene diacetate as oxidant has been developed. The reactions proceeded smoothly at room temperature under metal-free conditions and generate
POCl3-mediated reaction of 1-Acyl-1-carbamoyl Oximes: A new entry to cyanoformamides
Yang, Jiming,Xiang, Dexuan,Zhang, Rui,Zhang, Ning,Liang, Yongjiu,Dong, Dewen
supporting information, p. 809 - 811 (2015/03/18)
A facile and efficient one-pot synthesis of cyanoformamides was developed from readily available 1-acyl-1-carbamoyl oximes mediated by phosphoryltrichloride (POCl3) under mild conditions in good to high yields.
Tert-Butyl Hydroperoxide and Tetrabutylammonium Iodide-Promoted Free Radical Cyclization of α-Imino-N-arylamides and α-Azido-N-arylamides
Li, Dianjun,Yang, Tonghao,Su, Hailin,Yu, Wei
, p. 2529 - 2539 (2015/08/18)
The oxidizing system of tert-butyl hydroperoxide (TBHP) and tetrabutylammonium iodide (TBAI) is capable of generating α-(arylaminocarbonyl)iminyl radicals from ethyl 2-(N-arylcarbamoyl)-2-iminoacetates. These iminyl radicals preferably undergo intramolecular ipso attack on the benzene ring to give azaspirocyclohexadienyl radicals, which are readily captured by molecular oxygen under an oxygen atmosphere to yield azaspirocyclohexadienones. In the absence of oxygen, the reaction affords quinoxalin-2-one products. This oxidizing system is also effective to convert α-aryl-α-azido-N-arylamides to the corresponding iminyl radicals under basic conditions (sodium tert-butoxide, t-BuONa), and the subsequent cyclization of these iminyl radicals results in the formation of azaspirocyclohexadienone products in high yields under an oxygen atmosphere. Plausible mechanisms are proposed to rationalize the experimental results, and factors influencing the reactions are discussed.
Unexpected zirconium-mediated multicomponent reactions of conjugated 1,3-butadiynes and monoynes with acyl cyanide derivatives
Yu, Shasha,You, Xu,Liu, Yuanhong
supporting information, p. 13936 - 13940 (2013/01/15)
Going ber(zirc): Zirconium-butadiyne complexes react with acyl cyanide derivatives through diverse reaction pathways. The complexes react with two molecules of carbamoyl cyanide to form 1,4-benzodiazepin-2-one-derivatives containing azazirconacycles. Reac
Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere
Chiba, Shunsuke,Zhang, Line,Lee, Jian-Yuan
supporting information; experimental part, p. 7266 - 7267 (2010/08/05)
A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.
