An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition of N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve the products in excellent yields without requiring purification technique like column chromatography. All the synthesized compounds were evaluated for their in vivo anticonvulsant activity against maximal electroshock test. Six compounds showed maximum activity compared to the standard drug phenytoin. The scope of the new molecules as antimicrobial agents were tested against two bacterial strains (Staphylococcus aureus and Escherichia coli) and one fungal strain (Candida albicans).
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http://dx.doi.org/10.1016/j.bmcl.2011.04.117 | DOI Listing |
Org Biomol Chem
April 2022
Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
The atom transfer radical addition (ATRA) of bromodifluoroacetamides to arylalkynes and terminal alkenes was conducted using von Wangelin's Co catalyst system (CoBr/1,2-bis(diphenylphosphino)benzene/Zn) in acetone/HO at 30 °C to afford the corresponding functionalized difluoroacetamides in 33-89% yields. Moreover, the Co catalyst was successfully applied to the tandem addition/cyclization of 1,6-diene and -enyne substrates and intramolecular ATRA of -allyl and -propargyl bromodifluoroacetamides, significantly expanding the scope of radical difluoroalkylation.
View Article and Find Full Text PDFOrg Lett
August 2017
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
An efficient one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycosides has versatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars. Under reagent-free conditions, the N-allyl-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furnished cyclopropane-fused iminosugars.
View Article and Find Full Text PDFChem Commun (Camb)
July 2015
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
The rhodium-catalyzed reactions of 3-diazoindolin-2-imines with N,N-dialkylanilines, N-allyl-N-alkylanilines, and N-propargyl-N-alkylanilines and 3-diazoindolin-2-imines furnished 3-aryl-2-aminoindoles, 3-allyl-3-amino-2-iminoindolines, and tetrahydro-[1,4]diazepino[2,3-b]indoles, respectively. 3-Diazoindolin-2-imines acted as precursors of α-imino rhodium carbenes in these transformations.
View Article and Find Full Text PDFJ Org Chem
August 2013
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, USA.
A combination of experimental and computational methods has been used to understand the reactivity and selectivity of orthogonal thiol-ene and thiol-yne ″click″ reactions involving N-allyl maleimide (1) and N-propargyl maleimide (2). Representative thiols methyl-3-mercaptopropionate and β-mercaptoethanol are shown to add exclusively and quantitatively to the electron poor maleimide alkene of 1 and 2 under base (Et3N) initiated thiol-Michael conditions. Subsequent radical-mediated thiol-ene or thiol-yne reactions can be carried out to further functionalize the remaining allyl or propargyl moieties in near quantitative yields (>95%).
View Article and Find Full Text PDFBioorg Med Chem Lett
July 2011
Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, Tamil Nadu, India.
An operation friendly protocol for the synthesis of novel di(indolyl)indolin-2-ones via Cu(OTf)(2) catalyzed bis-addition of N-allyl and N-propargyl indole with isatin was developed. This methodology allowed us to achieve the products in excellent yields without requiring purification technique like column chromatography. All the synthesized compounds were evaluated for their in vivo anticonvulsant activity against maximal electroshock test.
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