Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1,4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu(OAc)2.
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http://dx.doi.org/10.1021/jo502582e | DOI Listing |
J Org Chem
December 2024
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. China.
Efficient synthesis of highly functionalized cyclopentenols with an exocyclic Z double bond was investigated via a (3 + 2) annulation reaction of 2-aroyl-D-A (donor-acceptor) cyclopropanes with alkynoates in the presence of DABCO. This synthetic approach featured a wide range of readily available 2-aroyl-substituted D-A cyclopropanes with diverse functional groups, densely substituted cyclopentenols with two stereogenic centers and an exocyclic double bond in a highly stereocontrolled manner and had operationally simple and mild reaction conditions.
View Article and Find Full Text PDFInt J Mol Sci
July 2024
Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, 44121 Ferrara, Italy.
Because of synergism between tubulin and HDAC inhibitors, we used the pharmacophore fusion strategy to generate potential tubulin-HDAC dual inhibitors. Drug design was based on the introduction of a -hydroxyacrylamide or a -hydroxypropiolamide at the 5-position of the 2-aroylbenzo[]furan skeleton, to produce compounds - and -, respectively. Among the synthesized compounds, derivatives , , , , and showed excellent antiproliferative activity, with IC values at single- or double-digit nanomolar levels, against the A549, HT-29, and MCF-7 cells resistant towards the control compound combretastatin A-4 (CA-4).
View Article and Find Full Text PDFThis report describes the visible-light-induced one-pot multicomponent regioselective synthesis of a series of 5-aroyl-3-((arylidene)amino)-2-((arylidene)hydrazono)-4-methyl-2,3-dihydrothiazoles as DNA and BSA targeting agents. The multicomponent condensation of thiocarbohydrazide and aldehydes with α-bromo-1,3-diketones, generated by the bromination of unsymmetrical 1,3-diketones with NBS using white LED light as an environmental friendly source in the presence of EtOAc solvent furnished the titled 2,3-dihydrothiazole derivatives in excellent yields. The exact regioisomeric structure was identified unambiguously by employing multinuclear 2D-NMR spectroscopy [H-C] HMBC; [H-C] HMQC and [H-N] HMBC.
View Article and Find Full Text PDFJ Org Chem
November 2023
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. China.
Acetic acid-catalyzed (3 + 2) cyclization reaction of substituted 2-aroyl-3-aryl-1,1-dicyanocyclopropanes with arylhydrazines was investigated for the efficient synthesis of 4-dicyanomethyl-1,3,5-triaryl-4,5-dihydropyrazoles in good yields, in which 4,5-double substituents are predominantly selective. This approach included the consecutive condensation, ring opening, and double nucleophilic cyclization reaction.
View Article and Find Full Text PDFChem Commun (Camb)
February 2023
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Aryne insertion reaction with 2-aroyl malonates/cyanoesters lead to the formation of diarylmethane or chromones depending on the substitution on the aryne ring. The presence of an electronegative atom at the position of arynes generates chromones, whereas other arynes lead to the formation of diarylmethanes, a cascade double aryne insertion.
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