2567-85-3Relevant articles and documents
Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
supporting information, p. 5815 - 5821 (2020/09/21)
We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.
Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: An efficient strategy for the synthesis of substituted 1-tosyl-1: H -pyrazoles
Zhang, Bang-Hong,Lei, Lin-Sheng,Liu, Si-Zhan,Mou, Xue-Qing,Liu, Wei-Ting,Wang, Shao-Hua,Wang, Jie,Bao, Wen,Zhang, Kun
supporting information, p. 8545 - 8548 (2017/08/04)
A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.
One-Pot Synthesis of Spirocyclic or Fused Pyrazoles from Cyclic Ketones: Calcium Carbide as the Carbon Source in Ring Expansion
Yu, Yue,Chen, Yang,Huang, Wei,Wu, Wanqing,Jiang, Huanfeng
, p. 9479 - 9486 (2017/09/23)
N-Tosylhydrazones generated in situ from cyclic ketones smoothly underwent a [3 + 2] cycloaddition to afford saturated spirocyclic pyrazoles and further transformed to the fused analogues via a ring expansion in certain cases. An inexpensive and renewable
Regioselective preparation of saturated spirocyclic and ring-expanded fused pyrazoles
Merchant, Rohan R.,Allwood, Daniel M.,Blakemore, David C.,Ley, Steven V.
, p. 8800 - 8811 (2015/01/08)
Saturated bicyclic pyrazoles represent an important class of biologically active molecules, but their preparation can be hampered by labor-intensive synthesis of required starting materials. A convenient one- or two-step procedure for the synthesis of sat
Catalytic three-component one-pot reaction of hydrazones, dihaloarenes, and amines
Roche, Maxime,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad
supporting information, p. 148 - 151 (2013/05/08)
A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and various primary and secondary amines was devised, producing nitrogen-containing 1,1'-diarylethylenes in good yields. The two C-C and C-N bonds formed through this
An efficient coupling of N-tosylhydrazones with 2-halopyridines: Synthesis of 2-α-styrylpyridines endowed with antitumor activity
Lawson, Marie,Hamze, Abdallah,Peyrat, Jean-Fran?ois,Bignon, Jér?me,Dubois, Joelle,Brion, Jean-Daniel,Alami, Mouad
, p. 3664 - 3673 (2013/06/26)
The synthesis of 2-α-styrylpyridines has been carried out by using the coupling of polyoxygenated N-tosylhydrazones with various 2-halopyridines. We demonstrated that the use of a catalytic amount of PdCl2(MeCN) 2 in combination with a bidentate ferrocene DPPF or a monodentate alkyl phosphine tBu2MeP-HBF4 constitutes an efficient protocol for this coupling, providing 2-α-styrylpyridines 2 in satisfactory to good yields. Among several polyoxygenated derivatives 2 evaluated, compound 2aa was found to exhibit excellent antiproliferative and antimitotic activities comparable to that of the reference compound isoCA-4. The Royal Society of Chemistry 2013.
N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C
Zhou, Lei,Liu, Zhenxing,Liu, Yizhou,Zhang, Yan,Wang, Jianbo
, p. 6083 - 6087 (2013/07/25)
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.
Transition-metal-free synthesis of pinacol alkylboronates from tosylhydrazones
Li, Huan,Wang, Long,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 2943 - 2946 (2012/04/18)
Highly efficient: Pinacol alkylboronates were synthesized by the reaction of tosylhydrazones with bis(pinacolato)diboron or pinacolborane under transition-metal-free conditions. This reaction represents an expeditious conversion of carbonyl functionality into a boronate group. Copyright
Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy
Wijtmans, Maikel,Verzijl, Dennis,van Dam, Cindy M.E.,Bosch, Leontien,Smit, Martine J.,Leurs, Rob,de Esch, Iwan J.P.
supporting information; scheme or table, p. 2252 - 2257 (2009/12/03)
A CXCR3 pocket capable of accommodating polycycloaliphatics was explored using a modular synthetic strategy. The systematic studies reveal that the tricyclic 2-adamantane and bicyclic (iso)bornyl group are efficiently recognized by CXCR3.
Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-[(E)-cycloalk-2-enylidenemethyl] thiolactomycin congeners
Ohata, Kohei,Terashima, Shiro
experimental part, p. 920 - 936 (2010/03/23)
The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure-activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2- enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.
