1613-94-1Relevant articles and documents
T3P-promoted synthesis of a series of novel 3-aryl-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones
Silverberg, Lee J.,Pacheco, Carlos,Sahu, Debashish,Scholl, Peter,Sobhi, Hany F.,Bachert, Joshua T.,Bandholz, Kaitlyn,Bendinsky, Ryan V.,Bradley, Heather G.,Colburn, Baylee K.,Coyle, David J.,Dahl, Jonathon R.,Felty, Megan,Fox, Ryan F.,Gonzalez, Kyanna M.,Islam, Jasra M.,Koperna, Stacy E.,Moyer, Quentin J.,Noble, Duncan J.,Ramirez, Melissa E.,Yang, Ziwei
, p. 1797 - 1805 (2020)
A series of 11 novel 3-aryl-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-aryl-C-phenyl imines with thiosalicylic acid. This provides simple and ready access to N-aryl compounds in this family, which have been generally difficult to prepare.
N-germyl derivatives of 4-nitrophenylamine: Germylamines, stable germa-imine
El Baz,Riviere-Baudet,Chazalette,Gornitzka
, p. 121 - 142 (2000)
N-germyl secondary amines of 4-nitrophenylamine were obtained by transamination from N-trialkylgermyldimethylamine, by transmetallation from the N-lithium derivative of 4-nitrophenylamine, or by intermolecular dehydrohalogenation between the corresponding halogermane and p-nitrophenylamine. Halogermylamines formed by the same methods are always obtained as a mixture with the corresponding diamine bis(4-nitrophenylamino)dimesitylgermane, and cannot be used as germa-imine precursors. However, elimination reactions from N-dimethylaminodimesitylgermyl-4-nitrophenylamine and N-dimesitylchlorogermyl-4-nitrophenylamine, formed from N-triethylgermyl N-dimesitylchlorogermyl-4-nitrophenylamine, yielded the thermally stable N-(4-nitrophenyl)dimesitylgerma-imine as a deep red amorphous powder. This germa-imine is moisture-sensitive, yielding (4-nitrophenylamino)dimesitylgermanol which adds to the germa-imine forming bis(4-nitrophenylaminodimesitylgermyl)oxide which was isolated as an orange powder. N-4-nitrophenyl)dimesitylgerma-imine adds readily to chloroform yielding N-dimesitylchlorogermyl-4-nitrophenylamine. The 3+2 addition of the germa-imine to N-t-butyl-phenylnitrone gave an adduct whose thermal decomposition began at 100°C yielding benzylidene-4-nitrophenylamine and dimesitylgermoxane. The germa-imine addition to 4,5-di-t-butyl ortho-quinone led to the corresponding dimesitylgermadioxolane through decomposition at room temperature of a transient adduct. The formation of isobutene in this reaction is constitent with a Single Electron Transfer mechanism in the first step.
Reaction of nitroanilines with aldehydes. Refinement of the Doebner–Miller reaction mechanism
Denisov, V. Ya.,Grishchenkova,Tkachenko,Luzgarev
, p. 1797 - 1803 (2016)
Due to intramolecular hydrogen bonding between the amino and nitro groups, o-nitroaniline is incapable of forming Schiff bases in the reactions with acetaldehyde and crotonaldehyde but is converted to quinoline derivative under Doebner–Miller reaction conditions via addition to the C=C double bond of the α,β-unsaturated aldehyde. Under analogous conditions, p-nitroaniline possessing a free amino group gives rise to the product of Doebner–Miller quinoline synthesis through intermediate formation of Schiff base dimer. The reaction of p-nitroaniline with benzaldehyde also yields the corresponding Schiff base, whereas o-nitroaniline is converted to N-benzyl derivative.
Vibrational spectra and Raman excitation profiles of some Schiff bases
Das, Radhendu,Kumar, Kamal
, p. 705 - 710 (1989)
The pre-resonance Raman spectra of three Schiff-base have been recorded and analysed.The theoretical Raman intensity factors have been calculated using ALBRECHT and HUTLEY's theory for pre-resonance enhancement and are compared with those of experimentally observed values.The assignments of the fundamental modes of vibration in the range 1300-1700 cm-1 have also been attempted on the basis of i.r. and Raman data.
Copper(II) triflate-sodium dodecyl sulfate catalyzed preparation of 1,2-diphenyl-2,3-dihydro-4-pyridones in aqueous acidic medium
Lanari, Daniela,Piermatti, Oriana,Pizzo, Ferdinando,Vaccaro, Luigi
, p. 2181 - 2184 (2012)
The reactions between N-benzylideneanilines and Danishefsky's diene proceed smoothly in acidic aqueous medium in the presence of a catalytic amount of copper(II) triflate-sodium dodecyl sulfate [Cu(OTf)2-SDS] to afford the corresponding 1,2-diphenyl-2,3-dihydro-4-pyridones in excellent yields of 84-95%. The aqueous solution containing the catalyst is recovered and reused without any loss in efficiency. Georg Thieme Verlag Stuttgart New York.
Photochemically Promoted Aza-Diels-Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
Arai, Noriyoshi,Ohkuma, Takeshi
, p. 7628 - 7636 (2017)
Aza-Diels-Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 °C), affording the cycloaddition product in 97% yield.
Triarylmethyl Cation-Catalyzed Three-Component Coupling for the Synthesis of Unsymmetrical Bisindolylmethanes
Bardelski, Kevin,Brindle, Cheyenne S.,Chen, Zhenghua,Guarino-Hotz, Melissa,Jones, Vanessa A.,Lucas, Kelly,Patterson, William J.
supporting information, p. 6737 - 6742 (2021/12/31)
An efficient synthesis of unsymmetrical bisindolylmethanes has been accomplished using triarylmethyl cations to catalyze the reaction of N-arylimines with two different indoles. Optimization of the organocatalyst by tuning cation stability allows for excellent single addition selectivity when coupled with p-nitrophenyl imines. The optimal catalyst is commercially available, and the reaction minimizes waste and environmental impact by employing a one-to-one ratio of starting materials. The intermediates can be isolated or used in situ in a one-pot two-step reaction to generate unsymmetrical bisindolylmethanes in high yields. The reaction tolerates a broad range of imines with the highest yields observed for electron-poor and neutral imines. A wide range of indole nucleophiles are also successfully employed allowing for the creation of a large variety of unsymmetrical bisindolylmethanes.
Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination
Ramachandran, P. Veeraraghavan,Choudhary, Shivani,Singh, Aman
, p. 4274 - 4280 (2021/03/09)
Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.
Cyclometalated Half-Sandwich Iridium(III) Complexes: Synthesis, Structure, and Diverse Catalytic Activity in Imine Synthesis Using Air as the Oxidant
Li, Rong-Jian,Ling, Chun,Lv, Wen-Rui,Deng, Wei,Yao, Zi-Jian
, p. 5153 - 5162 (2021/05/04)
Four air-stable cyclometalated half-sandwich iridium complexes 1-4 with C,N-donor Schiff base ligands were prepared through C-H activation in moderate-to-good yields. These complexes have been well characterized, and their exact structure was elaborated on by single-crystal X-ray analysis. The iridium(III) complexes 1-4 showed good catalytic activity in the imine synthesis under open-flask conditions (air as the oxidant) from primary amine oxidative homocoupling, secondary amine dehydrogenation, and the cross-coupling reaction of amine and alcohol. Substituents bonded on the ligands of the iridium complexes displayed little effect on the catalytic efficiency. The stability and good catalytic efficiency of the iridium catalysts, mild reaction conditions, and substrate universality showed their potential application in industrial production.
Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ
Xiong, Ruimei,Hussain, Muhammad Ijaz,Liu, Qing,Xia, Wen,Xiong, Yan
supporting information, (2019/12/11)
A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.
