7318-33-4Relevant academic research and scientific papers
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.
Divergent Synthesis of Vinyl-, Benzyl-, and Borylsilanes: Aryl to Alkyl 1,5-Palladium Migration/Coupling Sequences
Han, Jie-Lian,Ju, Cheng-Wei,Qin, Ying,Zhao, Dongbing
supporting information, p. 6555 - 6560 (2020/03/03)
Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through-space metal/hydrogen shifts allow functionalization of C?H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5-palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl-, benzyl-, and borylsilanes, constituting a unique C(sp3)?H transformation based on a 1,5-palladium migration process.
Metal-free and highly regioselective synthesis of N-heteroaryl substituted pyrazoles from α,β-unsaturated N-tosylhydrazones and heteroaryl chlorides
Zeng, Lin,Guo, Xiao-Qiang,Yang, Zai-Jun,Gan, Ya,Chen, Lian-Mei,Kang, Tai-Ran
supporting information, (2019/07/30)
A cascade cyclization/nucleophilic aromatic substitution (SNAr) reaction of α,β-unsaturated N-tosylhydrazones with N-heteroaryl chlorides was developed for the synthesis of N-heteroaryl pyrazole derivatives. This one-pot reaction provided bi(he
A base-promoted cascade reaction of α,β-unsaturated: N -tosylhydrazones with o -hydroxybenzyl alcohols: Highly regioselective synthesis of N-sec -alkylpyrazoles
Chen, Lian-Mei,Zhao, Juan,Xia, An-Jie,Guo, Xiao-Qiang,Gan, Ya,Zhou, Chuang,Yang, Zai-Jun,Yang, Jun,Kang, Tai-Ran
supporting information, p. 8561 - 8570 (2019/10/02)
An efficient method for the synthesis of N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcohols has been developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20:1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcohols, α,β-unsaturated N-tosylhydrazones and saturated N-tosylhydrazones also took place to afford pyrazoles in good yields. This reaction offers a new route to triarylmethanes with a simple operation and is applicable for large-scale synthesis.
One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles
Bzeih, Tourin,Zhang, Kena,Khalaf, Ali,Hachem, Ali,Alami, Mouad,Hamze, Abdallah
, p. 228 - 238 (2019/01/04)
A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.
Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
Wang, Chun-Ying,Han, Jia-Bin,Wang, Long,Tang, Xiang-Ying
, p. 14258 - 14269 (2019/11/11)
A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synt
Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C-P(O) Cleavage
Zhu, Jie,Mao, Mao,Ji, Huan-Jing,Xu, Jiang-Yan,Wu, Lei
supporting information, p. 1946 - 1949 (2017/04/28)
A palladium-catalyzed two-component coupling of allenylphosphine oxides with conjugated N-tosylhydrazones is revealed. For the first time, the cleavage of α-allenylic aryl ether toward pyrazolemethylene-substituted phosphinyl allenes enabled facile synthesis of combined motifs with pyrazole and allene. Moreover, the obtained adducts could be easily transformed to potential bioactive multifunctionalized phosphinates via a novel alkenyl C-P(O) cleavage.
Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct C - H Bond Functionalization
Xu, Shuai,Wu, Guojiao,Ye, Fei,Wang, Xi,Li, Huan,Zhao, Xia,Zhang, Yan,Wang, Jianbo
supporting information, p. 4669 - 4672 (2015/04/14)
The copper(I)-catalyzed alkylation of electron-deficient polyfluoroarenes with N-tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp2) - C(sp3) bonds with polyfluoroarenes through direct C - H bond functionalization. Mechanistically, copper(I) carbene formation and subsequent migratory insertion are proposed as the key steps in the reaction pathway.
Base-catalyzed N -N bond cleavage of hydrazones: Synthesis of α-amino ketones
Tang, Hai-Tao,Zhou, Yun-Bing,Zhu, Yu,Sun, Hong-Chao,Lin, Min,Zhan, Zhuang-Ping
supporting information, p. 1278 - 1281 (2014/05/06)
An efficient Cs2CO3-promoted synthesis of α-amino ketones using hydrazines, aldehydes, and α-haloketones as starting materials through a cascade condensation/nucleophilic substitution/N -N bond cleavage route is developed. The carbonyl group plays a key role in this novel N -N bond cleavage process. Breaking good: A novel method of base-catalyzed N -N bond cleavage of hydrazones has been discovered. A variety of α-amino ketones was synthesized using hydrazines, α-haloketones, and benzaldehyde as starting materials through a cascade condensation/ nucleophilic substitution/N -N bond cleavage sequence.
Efficient synthesis of 1,5-disubstituted carbohydrazones using K 2CO3 as a carbonyl donor
Wen, Jun,Yang, Chu-Ting,Jiang, Tao,Hu, Sheng,Yang, Tong-Zai,Wang, Xiao-Lin
supporting information, p. 2398 - 2401 (2014/05/20)
A novel reaction that generates 1,5-disubstituted carbohydrazones via the carbonylation of tosylhydrazones has been developed. For the first time, the inexpensive, readily available, environmentally friendly, and nongaseous potassium carbonate is used as
