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.
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.
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Khoo
, p. 993 (1979)
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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.
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.
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%.
