cas 55305-43-6, N-Cyano-N-phenyl-p-toluenesulfonaMide

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Rhodium(III)-catalyzed cyanation of vinylic C-H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent
Rh(iii)-catalyzed direct vinylic C-H cyanation reaction has been developed as a practical method for the synthesis of alkenyl nitriles. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation.
Su, Wei,Gong, Tian-Jun,Xiao, Bin,Fu, Yao
p. 11848 - 11851
(2015)
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A practical method for N-cyanation of secondary amines and sulfonamides
Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl)-N-arylsulfonyl-cyanamides, as the significant building blocks of the organic transformation.
Hang, Zhaojun,Li, Zuowa,Tong, Xiaowei,Wang, Zhao-yan,Xue, Weihua
(2022/02/07)

COMPOUNDS TARGETING PRMT5
Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
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Paragraph 0306

(2021/10/11)

Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides
The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.
Wang, Chuan-Chuan,Qu, Ya-Li,Liu, Xue-Hua,Ma, Zhi-Wei,Yang, Bo,Liu, Zhi-Jing,Chen, Xiao-Pei,Chen, Ya-Jing
p. 3546 - 3554
(2021/02/16)

Ni-Catalyzed Reductive Arylcyanation of Alkenes
We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.
Li, Hengxu,Chen, Jiachang,Dong, Jueqi,Kong, Wangqing
supporting information
p. 6466 - 6470
(2021/08/23)

A boron-nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones
Cyanation offers a simple method for the introduction of a nitrile group into organic molecules and an orthogonal route for the installation of a wide array of functional groups using simple transformations. Cyanation methods are dominated by transition metal catalysis and the use of hydrogen cyanide gas. Here, the electrophilic cyanation of enones was achieved using a main-group catalyst and a non-toxic, electrophilic cyanide source. This protocol was applied across a broad substrate scope including those containing reducible functional groups. Mechanistic studies indicated an amino-borane intermediate which underwent B-N transborylation (B-N/B-H exchange) to achieve catalytic turnover.
Benn, Kieran,Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
supporting information
p. 9406 - 9409
(2021/09/22)

COMPOUNDS TARGETING PRMT5
Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
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(2020/10/20)

Synthesis and Reactivity of N-Allenyl Cyanamides
N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.
Ayres, James N.,Williams, Matthew T.J.,Tizzard, Graham J.,Coles, Simon J.,Ling, Kenneth B.,Morrill, Louis C.
supporting information
p. 5282 - 5285
(2018/09/13)

Indole-3-carbonitriles as DYRK1A inhibitors by fragment-based drug design
Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer's disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3, 2-c]quinoline-6-carboxy
Meine, Rosanna,Becker, Walter,Falke, Hannes,Preu, Lutz,Loa?c, Nadège,Meijer, Laurent,Kunick, Conrad
supporting information

(2018/02/07)

Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)
The first one-pot deoxycyanamidation of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more commonly employed for electrophilic C- and N-cyanation processes.
Ayres, James N.,Ashford, Matthew W.,St?ckl, Yannick,Prudhomme, Vassili,Ling, Kenneth B.,Platts, James A.,Morrill, Louis C.
supporting information
p. 3835 - 3838
(2017/07/26)

The application of NCTS (N-cyano-N-phenyl-p-toluenesulfonamide) in palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides
Using NCTS (N-cyano-N-phenyl-p-toluenesulfonamide) as an electrophilic cyanation reagent, palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides was achieved under mild conditions. The method allowed the effective synthesis of various aryl nitriles in suitable yields via a coupling reaction.
Li, Jizhen,Xu, Wenbin,Ding, Junshuai,Lee, Kuo-Hsiung
supporting information
p. 1205 - 1209
(2016/03/01)

Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides
An unprecedented intermolecular cyclizative capture of the cyanamide anion and several nitrile oxides enables the synthesis of oxadiazol-5-imines.
Bhat, Shreesha V.,Robinson, David,Moses, John E.,Sharma, Pallavi
supporting information
p. 1100 - 1103
(2016/03/15)

Cobalt-Catalyzed Electrophilic Cyanation of Arylzinc Halides with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)
The cobalt-catalyzed cross-coupling of organozinc bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is described. The same cobalt catalyst, cobalt(II) bromide, was used for both the synthesis of the organozinc species and the cross-coupling reaction. However in this case, a catalytic amount of zinc dust is necessary in the second step to release the low-valent cobalt. Under these mild conditions, moderate to excellent yields of different benzonitriles were obtained.
Cai, Yingxiao,Qian, Xin,Rrat, Alice,Auffrant, Audrey,Gosmini, Corinne
supporting information
p. 3419 - 3423
(2016/01/25)

Rhodium-catalyzed directed C-H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide
A Rh-catalyzed directed C-H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this C-H cyanation process, and the reaction tolerates a variety of synthetically important functional groups.
Gong, Tian-Jun,Xiao, Bin,Cheng, Wan-Min,Su, Wei,Xu, Jun,Liu, Zhao-Jing,Liu, Lei,Fu, Yao
supporting information
p. 10630 - 10633
(2013/08/23)

A general rhodium-catalyzed cyanation of aryl and alkenyl boronic acids
Give me a cyanide: N-cyano-N-phenyl-p-methylbenzenesulfonamide as a cyanation reagent allows the synthesis of aryl(alkenyl) nitriles in good yield under mild conditions (see scheme; cod=cycloocta-1,5-diene). Combination of the procedure with the direct borylation of arenes and hydroboration of alkynes leads to the straightforward synthesis of various nitriles.
Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; experimental part
p. 519 - 522
(2011/03/16)

A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides
N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero)aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present methodology is shown by the expeditious syntheses of interesting pharmaceutical intermediates. Notably, chemoselective monocyanation of dibromoarenes is also achieved. Copyright
Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; experimental part
p. 4217 - 4222
(2011/05/06)