29665-24-5Relevant articles and documents
Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
Yang, Dong,Shi, Jingqi,Chen, Jiaming,Jia, Xiaoqi,Shi, Cuiying,Ma, Lifang,Li, Ziyuan
, p. 18966 - 18973 (2021/06/03)
Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp3)-C(sp3) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed.
Air-Induced One-Pot Synthesis of N-Sulfonylformamidines from Sulfonyl Chlorides, NaN3, and Tertiary/Secondary Amines
Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,Xia, Xiao-Yi,Chen, Xiao-Lan,Qu, Ling-Bo,Zhao, Yu-Fen
supporting information, p. 6071 - 6076 (2019/09/09)
An efficient and practical one-pot strategy for the synthesis of N-sulfonylformamidines was developed by directly using easily available sulfonyl chlorides, sodium azide and tertiary/secondary amines in the presence of 5 mol-% CuBr2 under aerob
N -Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of N -sulfonyl amidines
Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Luo, Dongping,Wang, Xinyan,Hu, Yuefei
supporting information, p. 8222 - 8225 (2018/07/29)
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from a 3-butyn-2-one participating CuAAC/ring-opening method. Its high reactivity due to bearing two EWGs allowed us to offer the first example of a reaction between ketenimine and amide to synthesize N-sulfonyl amidines efficiently.
CuCI/CCI4-Promoted Convenient Synthesis of Sulfonyl Amidines from Tertiary Amines and Sulfonyl Azides
Xu, Xiaoliang,Ge, Zhichuang,Cheng, Dongping,Lei, Ma.,Lu, Chunshan,Zhang, Qunfeng,Yao, Nan,Li, Xiaonian
supporting information; experimental part, p. 897 - 899 (2010/06/13)
Chemical Equation Presentation Promoted by CuCI/CCI4, a variety of sulfonyl azides and tertiary amines were successfully coupled to give sulfonyl amidine derivatives in good to excellent yields. A possible mechanism for this reaction Is discussed
An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide
Xu, Xiaoliang,Li, Xiaonian,Ma, Lei,Ye, Ning,Weng, Bojie
supporting information; experimental part, p. 14048 - 14049 (2009/03/11)
It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives. Copyright
N-(2,2,2-TRICHLOROETHYLIDENE)ARENESULFONAMIDES AND N-(2,2,2-TRICHLOROETHYLIDENE)ETHOXYFORMAMIDES IN REACTIONS WITH AMINES
Mirskova, A. N.,Levkovskaya, G. G.,Bryuzgin, A. A.,Drozdova, T. I.,Kalikhman, I. D.,Voronkov, M. G.
, p. 119 - 125 (2007/10/02)
The reaction of highly electrophilic N-(2,2,2-trichloroethylidene)arenesulfonamides with primary alkylamines and arylalkylamines leads to the formation of the addition products N-arenesulfonamides.These compounds are unstable, and this is due to the presence of the three electronegative substituents at the methine carbon atom.More basic dialkylamines lead to haloform decomposition of the N-(2,2,2-trichloroethylidene)arenesulfonamides and give high yields of dialkylarenesulfonylformamidines.At the same time dialkylamines add to N-(2,2,2-trichloroethylidene)etoxyformamide, forming N-ethoxyformamide.In reaction with trichloroethylideneethoxyformamide dimethylethanolamine forms the O-amidoalkylation product, i.e., N-ethoxyformamide, but its reaction with N-(2,2,2-trichloroethylidene)arenesulfonamide gives rise to its haloform decomposition with the formation of the corresponding arenesulfonamide.
