BITS Faculty Publications
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Item Copper(II)-Catalyzed Synthesis of Pyrrolo[3,4-b]quinolinediones from o-Amino Carbonyl Compounds and Maleimides(ACS, 2021-02) Kumar, AnilA copper(II)-catalyzed cascade synthesis of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones has been achieved from readily available o-amino carbonyl compounds and maleimides. This one-pot cascade strategy involves a copper-catalyzed aza-Michael addition followed by condensation and oxidation to deliver the target molecules. The protocol features a broad substrate scope and excellent functional group tolerance and affords products in moderate to good (44–88%) yields.Item A novel and short synthesis of naturally occurring 5-(3′-indolyl)oxazoles(Wiley, 2010-08-20) Kumar, Dalip; Kumar, AnilA novel, concise, and convenient synthesis of 5-(3′-indolyl)oxazoles using relatively benign reagent [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo]benezene has been described. The advantages of this procedure include operational simplicity, good yield, and avoidance of the use of toxic metalItem A simple and facile synthesis of amidoalkyl naphthols catalyzed by Yb(OTf)3 in ionic liquids(CSP, 2009-05-23) Khungar, Bharti; Kumar, AnilAn improved, simple, and facile synthesis of amidoalkyl naphthols by employing three-component one-pot condensation reaction of β-naphthol, aromatic aldehydes, and amides in ionic liquids using ytterbium triflate as a mild Lewis acid catalyst is described. Advantageously, amidoalkyl naphthols were obtained in high yield under eco-friendly, economical, and non-corrosive conditions, and the catalyst was recycled.Item An Efficient and Simple One-Pot Synthesis of β-Acetamido Ketones Catalyzed by Ytterbium Triflate in Ionic Liquid(Elsiever, 2008-12-18) Kumar, Anil; Khungar, BhartiYtterbium triflate immobilized in the ionic liquid [bmim][BF4] catalyzes the three-component coupling of aromatic aldehydes, enolizable ketones, and acetonitrile in the presence of acetyl chloride at room temperature to afford β-acetamido ketones in good yields. The catalyst can be recovered and recycled for subsequent reactions without any appreciable loss of efficiency.Item Cerium Triflate: An Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Carbonyl Compounds under Solvent-Free Conditions(CSIRO, 2009-08-26) Kumar, AnilA simple and efficient chemoselective thioacetalization of carbonyl compounds has been achieved using Ce(OTf)3 (10 mol-%) as a catalyst under solvent-free conditions. Advantages of the methodology include very short reaction times, excellent yields, the catalytic use of a water tolerant Lewis acid, and simple recovery and reuse of the catalyst.Item ChemInform Abstract: Exploration of the CuAAC Reaction for the Synthesis of Novel 3-(Triazol-1-yl)methyl-imidazo[1,2-a]pyridines(Wiley, 2013-03-14) Kumar, AnilThe archetypical CuAAC click chemistry is explored to assemble diverse 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines. The approach is simple, general, and environmentally benign to generate a library of novel triazolo-imidazo[1,2-a]pyridine derivatives in good yield (30–90%).Item K Pericherla, P Khedar, B Khungar, Anil Kumar, One-pot sequential C-N coupling and cross dehydrogenative couplings: Synthesis of novel azole fused imidazo[1,2-a]pyridines, Chem. Commun. 2013, 49, 2924-2926(RSC, 2013) Kumar, Anil; Khungar, BhartiAn efficient one-pot protocol has been developed using sequential C–N coupling and intramolecular dehydrogenative cross-couplings for the synthesis of azole fused imidazo[1,2-a]pyridine derivatives in good yields (62–78%).Item Synthesis of Pyrazolo[3,4-d]pyrimidine Derivatives and Evaluation of their Src Kinase Inhibitory Activities(ISCB, 2013) Kumar, AnilA series of pyrazolo[3,4-d]pyrimidine derivatives was synthesized and evaluated for the Src kinase inhibitory activities. Compound 6e and 10c exhibited inhibition of Src kinase with an IC50 value of 5.6 and 5.1 μM, respectively. Hydroxamate derivative 15a was found to be a metal-mediated inhibitor for human Csk with an IC50 value of 2.0 μM showing 56-fold selectivity over Src kinase inhibition.Item Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities(RSC, 2013) Kumar, AnilA simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazoles and 1,3,5-triarylpyrazolines in [bmim][PF6] ionic liquid mediated by Cu(OTf)2 is described. The reaction protocol gave 1,3,5-triarylpyrazoles in good to high yields (71–84%) via a one-pot addition–cyclocondensation between chalcones and arylhydrazines, and oxidative aromatization without the requirement for an additional oxidizing reagent. The catalyst can be reused for up to four cycles without much loss in the catalytic activity. The pyrazoles (4a–o) and pyrazolines (3a–n) were evaluated for their antiproliferative activity in SK-OV-3, HT-29, and HeLa human cancer cells lines. Among all the compounds, 3b inhibited cell proliferation of HeLa cells by 80% at a concentration of 50 μM.Item Synthesis and Biological Evaluation of 2-Arylamino-5- (3′-Indolyl)-1,3,4-Oxadiazoles as Potent Cytotoxic Agents(Wiley, 2013) Kumar, Anil; Kumar, DalipCoupling of two key scaffolds in medicinal chemistry, the indole and 1,3,4-oxadiazole ring systems, gave rise to 2-arylamino-5-(3′-indolyl)-1,3,4-oxadiazoles with IC50 values in the nanomolar range against a panel of tumor cell lines. Preliminary structure–activity relationship studies indicate potential for improved selectivity through further manipulation of the oxadiazole C-2 and C-5 positions.
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