1788-13-2Relevant academic research and scientific papers
Copper-Catalyzed Tandem Reaction of Terminal Alkynes and Sulfonyl Azides for the Assembly of Substituted Aminotriazoles
Zheng, Xuchun,Wan, Yanjun,Ling, Fei,Ma, Cheng
, p. 3859 - 3862 (2017)
A simple combination of CuI/LiOtBu/DMF enables the tandem Huisgen [3 + 2] cycloaddition/amidation reaction of terminal alkynes and sulfonyl azides to 5-sulfamide-1-(N-sulfonyl)-1,2,3-triazoles I, which can undergo an alkylation/desulfonation sequence to deliver highly substituted aminotriazoles II by one-pot or one-pot, two-step procedures.
Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
Cho, Seung Hwan,Yoo, Eun Jeong,Bae, Imhyuck,Chang, Sukbok
, p. 16046 - 16047 (2005)
It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mil
Novel Catalytic Three-Component Reaction between a Terminal Alkyne, Sulfonyl Azide, and O -Methyl Oxime
Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Barat-Seftejani, Forugh,Nouri, Azita
, p. 1445 - 1448 (2017)
O -Methyl oximes have been employed as nucleophiles in reactions with ketenimines derived from sulfonyl azides and terminal alkynes to form N -alkylidene N ′-tosylacetimidamide derivatives. The optimized conditions involved the use of CuPF 6 and i -Pr 2 NEt in MeCN at 65 °C. Both O -methyl aldoximes and ketoximes were tolerated under the optimum conditions.
Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
Sang, Dayong,Dong, Bingqian,Liu, Yunfeng,Tian, Juan
, p. 3586 - 3595 (2022/02/25)
The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec
Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives
Silva, Luana,Rosário, Alisson R.,Machado, Bianca M.,Lüdtke, Diogo S.
supporting information, (2020/12/25)
We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, sulfonamides, imides, phosphoramide and also carbamate.
Metal-free C-H Activation over Graphene Oxide toward Direct Syntheses of Structurally Different Amines and Amides in Water
Shukla, Prashant,Asati, Ambika,Bhardiya, Smita R.,Singh, Manorama,Rai, Vijai K.,Rai, Ankita
, p. 15552 - 15561 (2020/12/02)
Unprecedented metal-free synthesis of a variety of amines and amides is reported via amination of C(sp3)-H and C(sp2)-H bonds. The strategy involves graphene-oxide/I2-catalyzed nitrene insertion using PhINTs as a nitrene (NT) source in water at room temperature. A wide range of structurally different substrates, viz., cyclohexane, cyclic ethers, arenes, alkyl aromatic systems, and aldehydes/ketones, having an α-phenyl ring have been employed successfully to afford the corresponding nitrene insertion product in good yield, albeit low in few cases. The envisaged method has superiority over others in terms of its operational simplicity, metal-free catalysis, use of water as a solvent, ambient reaction conditions, and reusability of the catalyst.
Laboratory experiment: Synthesis and characterization of 4-methyl-N-(phenylacetyl)benzenesulfonamide through Cu(I)-catalysis
Jung, Byunghyuck
, p. 187 - 190 (2018/06/12)
A three-component coupling reaction of phenylacetylene, p-toluenesulfonyl azide, and water through copper catalysis is described to provide knowledge of spectroscopy and catalytic reactions and to introduce current research topics in organic chemistry for
DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature
Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
supporting information, p. 2681 - 2684 (2016/11/26)
An expeditious room temperature protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and substituted azides has been achieved using the combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid. This expeditious protocol is applicable to aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids the possible side reactions. Devoid of acetic acid, the reaction pathway alters to the ketinimine route and results in the formation of sulfonamides.
Titanium-Promoted Acylation of Sulfonamides to N -Acylsulfonamide PPAR Antagonists
Ammazzalorso, Alessandra,Tricca, Maria Luisa,Bruno, Isabella,De Filippis, Barbara,Di Matteo, Mauro,Fantacuzzi, Marialuigia,Giampietro, Letizia,Maccallini, Cristina,Mollica, Adriano,Amoroso, Rosa
supporting information, p. 2546 - 2554 (2015/11/28)
The direct acylation of sulfonamides by esters represents an attractive strategy in organic chemistry, being an interesting alternative to classical approaches to N-acylsulfonamides. Here is described a simple and effective method to obtain N-acylsulfonam
Benzyl anion transfer in the fragmentation of N-(phenylsulfonyl)-benzeneacetamides: a gas-phase intramolecular SNAr reaction
Shen, Shanshan,Chai, Yunfeng,Liu, Yaqin,Li, Chang,Pan, Yuanjiang
supporting information, p. 10205 - 10211 (2015/10/20)
In this study, we report a gas-phase benzyl anion transfer via intramolecular aromatic nucleophilic substitution (SNAr) during the course of tandem mass spectrometry of deprotonated N-(phenylsulfonyl)-benzeneacetamide. Upon collisional activati
