19350-72-2Relevant articles and documents
Potassium tert -Butoxide Promoted Synthesis of 4,5-Diaryl-2 H -1,2,3-triazoles from Tosylhydrazones and Nitriles
Qiu, Shanguang,Chen, Yuxue,Song, Xinming,Liu, Li,Liu, Xi,Wu, Luyong
supporting information, p. 86 - 90 (2020/11/02)
Intermolecular cycloaddition of tosylhydrazones with nitriles was investigated. t -BuOK was shown to be an excellent base for increasing the effectiveness of the reaction in this protocol, and homocoupling of the tosylhydrazones was significantly inhibited by using xylene as a solvent. Through this transformation, a variety of 4,5-diaryl-2 H -1,2,3-triazoles were prepared in good to excellent yields and with high purities. The process is azide-free and transition-metal-free.
Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes
Bian, Xue-Wei,Zhang, Ling,Shoberu, Adedamola,Zou, Jian-Ping
supporting information, (2021/04/02)
A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.
Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones
Wei, Zeyang,Zhang, Qi,Tang, Meng,Zhang, Siyu,Zhang, Qian
supporting information, p. 4436 - 4440 (2021/05/26)
The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 6784 - 6788 (2021/09/08)
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol
Zhu, Lei,Ren, Xiaojian,Yu, Yinghua,Ou, Pengcheng,Wang, Zhi-Xiang,Huang, Xueliang
supporting information, p. 2087 - 2092 (2020/03/04)
A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.
Blue Light-promoted Carbene Transfer Reactions of Tosylhydrazones
Xu, Yingying,Lv, Guanghui,Yan, Kaichuan,He, Hua,Li, Jianglian,Luo, Yi,Lai, Ruizhi,Hai, Li,Wu, Yong
supporting information, p. 1945 - 1947 (2020/06/08)
Metal-free photochemical carbene-transfer reactions of tosylhydrazones were developed under blue light irradiation at room temperature. This reaction constructs C?X (X=C, N, O, S) bonds and cyclopropanes from readily available and stable starting material
Acid-Promoted [3 + 1 + 1] Cyclization of N-Tosylhydrazones and Isocyanides: A Method for the Preparation of 4,5-Diaminopyrazoles
Zhang, Qian,Tang, Meng,Zhang, Siyu,Wei, Zeyang
supporting information, p. 5182 - 5186 (2020/07/04)
A facile method for the preparation of 4,5-diaminopyrazoles from N-tosylhydrazones and isocyanides was developed. The reaction was general for a wide range of substrates, and it demonstrated excellent tolerance to a variety of substituents. More important
Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells
Deng, Jiajie,Guo, Guiling,Wu, Xueting,Yu, Zhipeng,Zhao, Xiaohu
supporting information, p. 5602 - 5607 (2020/08/21)
A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained NN double bond as a dipolarophile was discovered. The photo-isomerization of carbon-bridged octocyclic azobenzene (CBOA) into its trans-configuration accelerates the ligation reaction at a very rapid rate (28 400 M-1 s-1). The CBOA-based photo-click reaction was proved to be bioorthogonal. In addition, the NoxaB peptide was successfully cross-linked by a CBOA stapler which plays a dual role: Photo-control of the conformation of the peptide and photo-conjugation of probes in live cells.
Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-a]quinolines
Jiang, Yubo,Ren, Yongsheng,Xiao, Tiebo,Xiong, Shaoqi,Yang, Jianhua
supporting information, p. 7174 - 7182 (2020/10/02)
In this paper, a tandem reaction involving copper-catalyzed cross-coupling and allene-mediated cyclization of 1-(2-ethynylaryl)-1,4-disubstituted-1,2,3-triazole withN-tosylhydrazone has been developed. This method features operational simplicity, excellen
