73318-99-7Relevant academic research and scientific papers
N-alkylation using sodium triacetoxyborohydride with carboxylic acids as alkyl sources
Tamura, Satoru,Sato, Keigo,Kawano, Tomikazu
, p. 101 - 103 (2018/01/05)
A versatile N-alkylation was performed using sodium triacetoxyborohydride and carboxylic acid as an alkyl source. The combination of these reagents furnished products different from those given previously by a similar reaction. Moreover, the mild conditions of our method allowed some functional groups to remain through the reaction, whereas they would react and be converted into other moieties in the similar reductive N-alkylation reported previously. Herein, we provide a new procedure for the preparation of various compounds containing nitrogen atoms.
Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst
Lucas, Katherine M.,Kleman, Adam F.,Sadergaski, Luke R.,Jolly, Caitlyn L.,Bollinger, Brady S.,Mackesey, Brittany L.,McGrath, Nicholas A.
supporting information, p. 5774 - 5778 (2016/07/06)
A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.
Gold catalysis coupled with visible light stimulation: Syntheses of functionalized indoles
Cai, Shunyou,Yang, Kai,Wang, David Zhigang
supporting information, p. 2606 - 2609 (2014/06/09)
A judicious combination of Au-catalysis and synergistic visible-light stimulation formulates an exceptionally simple and mild reaction system capable of directly coupling anilines and alkynes to form multifunctionalized indoles.
Aerobic oxidative N-dealkylation of tertiary amines in aqueous solution catalyzed by rhodium porphyrins
Ling, Zhen,Yun, Lin,Liu, Lianghui,Wu, Bing,Fu, Xuefeng
supporting information, p. 4214 - 4216 (2013/05/22)
Aerobic oxidative N-dealkylation of a variety of aliphatic tertiary amines and anilines catalyzed by rhodium(iii) tetra (p-sulfonatophenyl) porphyrin ((TSPP)RhIII) is achieved in aqueous solution using dioxygen as the sole oxidant.
Synthesis of new 1-[4-methane(amino)sulfonylphenyl]-5-[4-(aminophenyl)]-3- trifluoromethyl-1H-pyrazoles
Abdellatif, Khaled R. A.,Chowdhury, Morshed A.,Knaus, Edward E.
experimental part, p. 1707 - 1710 (2009/09/08)
(Chemical Equation Presented) A regiospecific cyclization-dehydration reaction of a 1-[4-(N-alkyl-N-(tert-butyloxycarbonyl)amino)-phenyl]-4,4,4- trifluorobutane-1,3-done with a 4-aminosulfonyl-, or 4-methylsulfonyl-, phenylhydrazine hydrochloride in refluxing ethanol proceeded with simultaneous loss of the N-tert-butyloxycarbonyl protecting group to afford a group of 1-(4-methanesulfonylphenyl or 4-aminosulfonylphenyl)-5-[4-(N-alkylaminophenyl)]- 3-(trifluoromethyl)-1H-pyrazoles (6). Subsequent reaction of the pyrazole 6 (R1 = R2 = Me) with nitric oxide (40 psi) proceeded via a N-methylamino-N-diazen-1-ium-1,2-diolate intermediate that undergoes protonation of the more basic diazen-1-ium-1,2-diolate N2-nitrogen and then loss of a nitroxyl (HNO) species to furnish the N-nitroso product 7.
2-Hydroxymethyl-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl] -1-benzenesulfonamide (DRF-4367): An orally active COX-2 inhibitor identified through pharmacophoric modulation
Singh, Sunil Kumar,Vobbalareddy, Saibaba,Kalleda, Srinivasa Rao,Rajjak, Shaikh Abdul,Casturi, Seshagiri Rao,Datla, Srinivasa Raju,Mamidi, Rao N.V.S.,Mullangi, Ramesh,Bhamidipati, Ravikanth,Ramanujam, Rajagopalan,Akella, Venkateswarlu,Yeleswarapu, Koteswar Rao
, p. 2442 - 2450 (2007/10/03)
Analogs of 1,5-diarylpyrazoles with a novel pharmacophore at N1 were designed, synthesized and evaluated for the in-vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The variations at/around position-4 of the C-5 phenyl ring in conjunction with a CF3 and CHF2 groups at C-3 exhibited a high degree of potency and selectivity index (SI) for COX-2 inhibition. The in-vivo evaluation of these potent compounds with a few earlier ones indicated the 4-OMe-phenyl analog 6 and the 4-NHMe-phenyl analog 9 with a CF3, and the 4-OEt-phenyl analog 19 with a CHF2 group at C-3 to possess superior potency than celecoxib. In addition to its impressive anti-inflammatory, antipyretic, analgesic and anti-arthritic properties, compound 6 (DRF-4367) was found to possess an excellent pharmacokinetic profile, gastrointestinal (GI) safety in the long-term arthritis study and COX-2 potency in human whole blood assay. Thus, compound 6 was selected as an orally active anti-inflammatory candidate for pre-clinical evaluation.
