- Synergy of anodic oxidation and cathodic reduction leads to electrochemical deoxygenative C2 arylation of quinoline: N-oxides
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The first example of electrochemical deoxygenative C2 arylation of quinoline N-oxides using sulfonyl hydrazines was demonstrated in this work. By employing both anodic oxidation and cathodic reduction, a variety of 2-arylquinolines were synthesized under metal catalyst-, exogenous-oxidant-, and exogenous-reductant-free conditions.
- Yuan, Yong,Jiang, Minbao,Wang, Tao,Xiong, Yunkui,Li, Jun,Guo, Huijiao,Lei, Aiwen
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supporting information
p. 11091 - 11094
(2019/09/20)
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- Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C?N/C?S Bond Formation in Allylic Surrogates
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Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand-controlled, Pd-catalyzed allylic substitution allowing for either selective C?N or C?S bond formation using vinylethylene carbonates (VECs) and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, divergent route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance, and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent π-allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles.
- Deng, Lei,Kleij, Arjan W.,Yang, Weibo
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supporting information
p. 19156 - 19161
(2018/11/30)
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- Synthesis of sulfonylhydrazone- and acylhydrazone-substituted 8-ethoxy-3-nitro-2h-chromenes as potent antiproliferative and apoptosis inducing agents
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3-Nitro-2H-chromenes have recently been identified as a novel class of potent antitumor agents. In view of the favorable effects shown by sulfonylhydrazones and acylhydrazones, we designed and synthesized a series of sulfonylhydrazone- and acylhydrazone-substituted 8-ethoxy-3-nitro-2H-chromene derivatives, and evaluated their cell growth inhibition activities against A549, KG-1, A2780, and K562 cells. All the tested compounds exhibited more potent antiproliferative activity than BENC-511 against KG-1 cells. These compounds displayed IC50 values in the nanomolar range against A2780 cells. Compound 7d showed prominent cytotoxicity against K562 cells with an IC 50 of 0.11 μM, which was comparable to that of BENC-511. Compound 7d arrested K562 cells at the G1 phase at high concentrations and induced apoptosis in K562 cells. Furthermore, 7d increased the levels of cleaved caspase-3, decreased the expression of bcl-2 and induced the cleavage of poly(ADP-ribose) polymerase in K562 cells. Thus, this study provides the development of a series of novel compounds as effective antitumor agents with apoptotic death ability.
- Zhang, Datong,Ma, Yuntong,Liu, Yu,Liu, Zhao-Peng
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p. 576 - 588
(2014/08/18)
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- SOME REACTIONS OF PYRIDINE-3-SULFONYL CHLORIDE
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The hydrochloride of pyridine-3-sulfonyl chloride (1) with hydrazine gave the hydrazide (2), from which a semicarbazide (15) and a series of hydrazones (4-14) were obtained.The chemical shifts of the NH protons of the hydrazones were correlated with the Hammett ?-constants of the substituents.With sodium azide, the sulfonyl chloride (1) gave the azide (16) which reacted with both norbornene and triphenylphosphine.The sulfonyl chloride (1) was hydrolysed to the sulfonic acid (3) by boiling with ethanol.Reaction of the hydrazide (2) with β-diketones afforded the pyrazoles (19a-22a).The intermediate sulfonohydrazones (19-22) were isolated in each case; however the product with ethyl acetoacetate (26) could not be cyclised to the pyrazole.The mass spectra of the pyrazoles are briefly discussed.
- Cremlyn, Richard J.,Jones, Graham P.,Swinbourne, Fred J.,Yung, Kin
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p. 189 - 196
(2007/10/02)
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