- The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines
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A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.
- Chen, Fan,Cheng, Jiang,Qian, Peng-Cheng,Wang, Lu
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supporting information
(2021/12/17)
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- Rhodium-Catalyzed Reaction of Azobenzenes and Nitrosoarenes toward Phenazines
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A rhodium-catalyzed annulative reaction between azobenzenes and nitrosoarenes has been developed, leading to a series of phenazines in moderate to good yields. This procedure proceeds with sequential chelation-assisted addition of aryl C-H to nitrosoarenes and ring closure by electrophilic attack of azo group to aryl. During this transformation, the azo group served as not only a traceless directing group but also a building block in the final products.
- Xiao, Yan,Wu, Xiaopeng,Wang, Hepan,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 2565 - 2568
(2019/04/30)
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- Rh(III)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C-H functionalization enabled by a transient directing group
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A Rh(iii)-catalyzed bilateral cyclization was developed for the efficient construction of acridines proceeding with C-H functionalization whereby in situ formation and removal of an imino transient directing group in the presence of catalytic amount of BnNH2 are achieved. In this transformation, a sequential Rh(iii)-catalyzed C-H amination, cyclization, and aromatization process was involved.
- Hu, Weiming,Zheng, Qingheng,Sun, Song,Cheng, Jiang
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supporting information
p. 6263 - 6266
(2017/07/07)
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- Synthesis, characterization and applicability of three isotope labeled azobenzene photoswitches
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We describe a short, efficient approach for the synthesis of three novel isotope labeled azobenzene photoswitches. The synthesis is based on commercially available fully isotope labeled precursors. The target molecules have been obtained in good yields, c
- Pfister, Rolf,Ihalainen, Janne,Hamm, Peter,Kolano, Christoph
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scheme or table
p. 3508 - 3517
(2009/02/05)
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- Reaction of aromatic nitroso compounds with chemical models of 'thiamine active aldehyde'
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Aromatic nitroso compounds in the presence of base and 2-(α-hydroxyalkyl)-3,4-dimethylthiazolium trifluoromethanesulfonate and related salts furnish in variable yields O- and N-acyl-aryl hydroxylamines and 3,4-dimethylthiazolium trifluoromethanesulfonate. A primary kinetic isotope effect of 4.9, obtained for the appropriate 2α-deuterated thiazolium salt, points to the C2α-H bond cleavage as the rate determining step. Radical species detected by ESR were unambiguously identified as phenylhydronitroxide, but attempted trapping of the corresponding C-heterocyclic radicals by TEMPO was not successful, and substrates incorporating a potential cyclopropyl radical clock gave products with the cyclopropyl ring intact. Theoretical calculations revealed a large activation energy for such reaction, which thus cannot per se exclude the intervention of such radical species. Evidence for the likely operation of two concurrent mechanisms, a radical and a preponderant ionic pathway, involving the conjugate base of the thiazolium salt, as the chemical model for 'active thiamine', and ArNO is presented for the formation of the products of the reaction.
- Ferreira, Luísa M.,Marques, M. Manuel B.,Glória, Paulo M.C.,Chaves, Humberto T.,Franco, Jo?o-Pedro P.,Mourato, Isabel,Antunes, José-Rafael T.,Rzepa, Henry S.,Lobo, Ana M.,Prabhakar, Sundaresan
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p. 7759 - 7770
(2008/12/21)
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- REACTION BETWEEN Δ2-OXAZOLIN-5-ONES AND NITROSOBENZENE. FORMATION OF 1,2,4-OXADIAZOLINES
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2,4-diphenyl- and 2-p-methylphenyl-4-phenyl-Δ2-oxazolin-5-ones react at 80-110 deg C with nitrosobenzene to give benzamidines.However, reactions conducted at room temperature afford in high yield, the heretofore undescribed Δ4-oxadiazolin-3-carboxylic acids by regiospecific 1,3-dipolar cycloaddition.Thermal decomposition of the oxadiazolinecarboxylic acids gives the corresponding benzamidines.
- Rodriguez, H.,Pavez, H.,Marquez, A.,Navarrete, P.
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