- Potassium tert -Butoxide Promoted Synthesis of 4,5-Diaryl-2 H -1,2,3-triazoles from Tosylhydrazones and Nitriles
-
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.
- Qiu, Shanguang,Chen, Yuxue,Song, Xinming,Liu, Li,Liu, Xi,Wu, Luyong
-
supporting information
p. 86 - 90
(2020/11/02)
-
- Synthesis of 1 H-Pyrazol-5-yl-pyridin-2-yl-[1,2,4]triazinyl Soft-Lewis Basic Complexants via Metal and Oxidant Free [3 + 2] Dipolar Cycloaddition of Terminal Ethynyl Pyridines with Tosylhydrazides
-
Soft-Lewis basic complexants that facilitate chemoselective separation of the minor actinides from the lanthanides are critical to the closure of the nuclear fuel cycle. Complexants that modulate covalent orbital interactions with relevant metals of inter
- Veerakanellore, Giri Babu,Smith, Caris M.,Vasiliu, Monica,Oliver, Allen G.,Dixon, David A.,Carrick, Jesse D.
-
p. 14558 - 14570
(2019/11/11)
-
- Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N-tosylhydrazones under metal-free conditions
-
A metal-free cyclopropanation of electron-deficient olefins 3-substituted-2-cyanoacrylamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides wit
- Nie, Xufeng,Wang, Yachuan,Yang, Lijun,Yang, Zaijun,Kang, Tairan
-
supporting information
p. 3003 - 3007
(2017/07/17)
-
- Iron(III) phthalocyanine-chloride-catalyzed synthesis of sulfones from sulfonylhydrazones
-
In this study, sulfones are synthesized from sulfonylhydrazones catalyzed by iron(III) phthalocyanine chloride. This reaction offers broad substrate scope, occurs under mild conditions, utilized readily available reactants, and forms products in good-to-h
- Zhao, Jun-Long,Guo, Shi-Huan,Qiu, Jun,Gou, Xiao-Feng,Hua, Cheng-Wen,Chen, Bang
-
supporting information
p. 2375 - 2378
(2016/05/19)
-
- Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes
-
A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.
- Gao, Yang,Xiong, Wenfang,Chen, Huoji,Wu, Wanqing,Peng, Jianwen,Gao, Yinglan,Jiang, Huanfeng
-
p. 7456 - 7467
(2015/08/18)
-
- Synthesis of terminal allenes through copper-mediated cross-coupling of ethyne with N-tosylhydrazones or α-diazoesters
-
Ethyne is employed as coupling partner in coppermediated cross-coupling reactions with N-tosylhydrazones and α-diazoacetate, leading to the development of a new synthetic method for terminal allenes. With this novel coupling method, the terminal allenes w
- Ye, Fei,Wang, Chengpeng,Ma, Xiaoshen,Hossain, Mohammad Lokman,Xia, Ying,Zhang, Yan,Wang, Jianbo
-
p. 647 - 652
(2016/09/12)
-
- Facile one-pot synthesis of N-alkylated benzimidazole and benzotriazole from carbonyl compounds
-
An efficient one-pot N-alkylation of benzimidazole and benzotriazole from carbonyl compounds and tosylhydrazide has been accomplished via copper powder-catalyzed N - H bond insertion affording N-alkylated products in good yields. The reaction can tolerate a wide range of carbonyl compounds, such as aryl, alkyl, heterocyclic and α,β-unsaturated ketones, and aldehydes.
- Meng, Xu,Li, Xiaolong,Chen, Wenlin,Zhang, Yuanqing,Wang, Wen,Chen, Jinying,Song, Jinli,Feng, Huijie,Chen, Baohua
-
p. 349 - 356
(2014/04/17)
-
- Efficient synthesis of 1,5-disubstituted carbohydrazones using K 2CO3 as a carbonyl donor
-
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
- Wen, Jun,Yang, Chu-Ting,Jiang, Tao,Hu, Sheng,Yang, Tong-Zai,Wang, Xiao-Lin
-
supporting information
p. 2398 - 2401
(2014/05/20)
-
- An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
-
A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
-
p. 34764 - 34767
(2014/11/08)
-
- An efficient one-pot synthesis of 3,5-diaryl-4-bromopyrazoles by 1,3-dipolar cycloaddition of in situ generated diazo compounds and 1-bromoalk-1-ynes
-
A simple, highly efficient, one-pot synthesis of 3,5-di-aryl-4- bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and gem-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3H-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1H-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient-substituents on the aromatic ring of the hydrazones or the gem-dibromoalkenes gave desired products in moderate to good yields (67-86%). Georg Thieme Verlag Stuttgart - New York.
- Sha, Qiang,Wei, Yunyang
-
supporting information
p. 413 - 420
(2013/03/14)
-
- N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C
-
A mild and efficient method for the deoxygenative hydrogenation of aldehydes and ketones has been developed. The reaction is mediated by N-tosylhydrazine with H2 (1 atm) as the reductant and 10% Pd/C as the catalyst.
- Zhou, Lei,Liu, Zhenxing,Liu, Yizhou,Zhang, Yan,Wang, Jianbo
-
p. 6083 - 6087
(2013/07/25)
-
- Synthesis of allyl allenes through three-component cross-coupling reaction of N-tosylhydrazones, terminal alkynes, and allyl halides
-
Three's a crowd: Tri- and tetrasubstituted allyl allenes can be easily accessed by this CuI-catalyzed three-component coupling reaction of N-tosylhydrazones, terminal alkynes, and allyl halides. The reaction proceeds through a mechanism involving copper carbene migratory insertion.
- Ye, Fei,Hossain, Mohammad Lokman,Xu, Yan,Ma, Xiaoshen,Xiao, Qing,Zhang, Yan,Wang, Jianbo
-
supporting information
p. 1404 - 1407
(2013/07/26)
-
- Reductive azidation of carbonyl compounds via tosylhydrazone intermediates using sodium azide
-
Simple and direct: Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K2CO3, tetrabutylammonium bromide
- Barluenga, Jose,Tomas-Gamasa, Maria,Valdes, Carlos
-
supporting information; experimental part
p. 5950 - 5952
(2012/07/03)
-
- Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones
-
A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.
- Miao, Wenjun,Gao, Yuzhen,Li, Xueqin,Gao, Yuxing,Tang, Guo,Zhao, Yufen
-
p. 2659 - 2664
(2013/01/15)
-
- Copper-catalyzed nitrogen loss of sulfonylhydrazones: A reductive strategy for the synthesis of sulfones from carbonyl compounds
-
Figure Presented. An efficient method for the synthesis of sulfones via nitrogen loss of sulfonyl hydrazones is described. The reaction was performed in the presence of simple copper salt and base by utilization of sulfonyl hydrazones, which were easily p
- Feng, Xing-Wen,Wang, Jian,Zhang, Ji,Yang, Jing,Wang, Na,Yu, Xiao-Qi
-
supporting information; experimental part
p. 4408 - 4411
(2010/12/19)
-
- Tetraethylammonium bromide catalysed phase transfer reaction of potassium superoxide with hydrazones and tosylhydrazones
-
A variety of hydrazones and tosylhydrazones of carbonyl compounds have been investigated under the mild reaction conditions of potassium superoxide and tetraethylammonium bromide in dry dimethylformamide. As a result, hydrazones are generally transformed to their corresponding azines whereas tosylhydrazones undergo facile fragmentation to give the olefinic products in fairly good yields. The study highlights the use of tetraethylammonium bromide as an efficient and inexpensive catalyst for superoxide studies.
- Kumar,Singh
-
p. 579 - 583
(2007/10/03)
-
- Methylenecyclopropane Rearrangement as a Probe for Free Radical Substituent Effects. ?. Values for Commonly Encountered Conjugating and Organometallic Groups
-
A series of 3-aryl-2,2-dimethylmethylenecyclopropanes, 8, with NO2, NMe2, vinyl, isopropenyl, phenyl, cyclopropyl, CH2SiMe3, SiMe3, SnMe3, , and HgCl substitution in the para position of the aromatic ring have been prepared.All rearrange thermally to the corresponding isopropylidenecyclopropanes 9 at rates that are substituent dependent.These commonly encountered substituents all enhance rearrangement rates relative to the unsubstituted analogue with p-NMe2 being the most effective.The rate enhancements are interpreted in terms of stabilization of the biradical intermediate by the para substituent.Rate data have allowed the assignment of ?. values for these groups, which have not been previously determined.The nitro group in the para position is also quite effective in increasing the rearrangement rate, which contrasts with the effect of this group on many other free radical reactions.Vinyl is somewhat more effective as a radical stabilizing group than is isopropenyl or phenyl, possibly due to steric interactions in the planar conformations necessary for conjugative stabilization by isopropenyl or phenyl.Trimethylsilyl,trimethylstannyl, and HgCl all enhance the methylenecyclopropane rearrangement rate, but only to a moderate extent.Boron containing substituents, where boron can act as an acceptor group, are among the more effective radical stabilizing groups, as implied by their effect on the rearrangement rate of 8.The cyclopropyl and CH2SiMe3 groups, which also enhance the rearrangement rate of 8 to a moderate extent, become even more effective radical stabilizing groups when present in conjunction with the carbethoxy group.These two conjugating groups are therefore capable of acting as donor groups in captodative radical stabilization.
- Creary, Xavier,Mehrsheikh-Mohammadi, M. E.,McDonald, Steven
-
p. 3254 - 3263
(2007/10/02)
-