3968-10-3Relevant academic research and scientific papers
3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature
Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth
supporting information, (2019/12/30)
Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.
A microwave-assisted approach to N-(2-nitrophenyl)benzenesulfonamides that enhanced peroxidase activity in response to excess cadmium
Huang, Zhi-You,Liu, Min,Mao, Yi-Jun,Chen, Yu-De,Wang, Yan-Ping,Liu, Chong
supporting information, p. 626 - 629 (2019/02/01)
A facile and efficient approach to N-(2-nitrophenyl) benzenesulfonamides was developed under microwave irradiation. A series of pyrabactin analogues containing nitrophenyl scaffold was obtained in excellent yields. In addition, the method was pretty suitable to prepare flusulfamide. Significantly, the 3ae could enhance POD activity in response to heavy metal stress.
Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions
Vinayak, Botla,Chandrasekharam, Malapaka
supporting information, p. 3528 - 3531 (2017/07/17)
An unprecedented copper-catalyzed in situ azidation-oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr-H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.
Direct oxidative nitration of aromatic sulfonamides under mild conditions
Li, Ying-Xiu,Li, Lian-Hua,Yang, Yan-Fang,Hua, Hui-Liang,Yan, Xiao-Biao,Zhao, Lian-Biao,Zhang, Jin-Bang,Ji, Fa-Jin,Liang, Yong-Min
supporting information, p. 9936 - 9938 (2014/08/18)
A direct nitration of aromatic sulfonamides using sodium nitrite as the nitrating agent has been developed. The reaction shows typically mono-substitution selectivity and can be enlarged to the gram scale with good yield.
Chemoselective nitration of aromatic sulfonamides with tert-butyl nitrite
Kilpatrick, Brenden,Heller, Markus,Arns, Steve
supporting information, p. 514 - 516 (2013/02/25)
A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially reactive functionalities.
REACTION OF N-ARYLSULFONAMIDES WITH NITROSATING AGENTS
Zakatov, V. V.,Dubina, V. L.,Gladshtein, I. Ya.
, p. 540 - 542 (2007/10/02)
Only the mononitro derivatives are formed by the action of nitrosating agents on N-arylsulfonamides containing halogen atom and alkoxy and alkyl groups in the amide ring.The nature of the effect and the directing action of the substituents are discussed a
