- Silver nanoparticle-catalysed phenolysis of epoxides under neutral conditions: Scope and limitations of metal nanoparticles and applications towards drug synthesis
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Chemo- and regio-selective epoxide phenolysis is reported for the first time under neutral condition catalysed by silver nanoparticles. Other metal nanoparticles (e.g., Au, Pd, Cu, In, and Ru) are less effective. The choice of solvent is critical with 2-propanol being the best followed by DEF. Amongst various stabilisers used (surfactants, PEGs, tetra-alkylammonium halides) the tetra-alkylammonium halides are found to be the most effective (TBAF > TBAB > TBACl > TBAI). The role of the silver nanoparticles is envisaged as synchronous mode epoxide-phenol dual activation via a cooperative network of coordination, anion-π interaction, and hydrogen bond. The silver nanoparticles are recovered and reused for five consecutive times. The reaction has been used for the synthesis of propranolol and naftopidil as a few representative cardiovascular drugs.
- Seth, Kapileswar,Roy, Sudipta Raha,Kommi, Damodara N.,Pipaliya, Bhavin V.,Chakraborti, Asit K.
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p. 164 - 172
(2014/06/23)
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- Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
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Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-π interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.
- Seth, Kapileswar,Roy, Sudipta Raha,Pipaliya, Bhavin V.,Chakraborti, Asit K.
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supporting information
p. 5886 - 5888
(2013/07/25)
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- Novel bis- and tris-1,2,4-trioxanes: Synthesis and antimalarial activity against multidrug-resistant Plasmodium yoelii in swiss mice
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A new series of bis-1,2,4-trioxanes 12a-h, 13a-h, and 14a-h and tris-1,2,4-trioxanes 12i-14i were prepared and evaluated against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Cyclopentane-based bis-trioxanes 12a, 12b, 12f-h and cycloh
- Singh, Chandan,Verma, Ved Prakash,Naikade, Niraj Krishna,Singh, Ajit Shankar,Hassam, Mohammad,Puri, Sunil K.
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experimental part
p. 7581 - 7592
(2009/11/30)
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- Synthesis and antifungal activity of 1,3-bis<2- or 4-(substituted cinnamoyl or 1-acyl-4,5-dihydro-5-substituted phenyl-1H-pyrazol-3-yl)phenoxy-2-propanols and related compounds
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Condensation of 1,3-bis(2- or 4-acetylphenoxy or 2-acetyl-3-hydroxyphenoxy)-2-propanol (IIa-c), prepared from 2- or 4-hydroxy- or 2,6-dihydroxyacetophenone (Ia-c) and chloromethyloxirane, with substituted benzaldehydes gives the corresponding 1,3-bis-2-propanols (IIIa-i).Isomerization of the phenols IIIg-i with silica gel in solid phase furnishes the corresponding 1,3-bis(2-aryl-2,3-dihydro-4-oxo-4H-1-benzopyran-5-yloxy)-2-propanols (IVa-c).Condensation of IIIa-i with hydrazine in refluxing formic or acetic acid affords thecorresponding substituted 1,3-bis(2- or 4-(1-acyl-4,5-dihydro-5-substituted phenyl-1H-pyrazol-3-yl)phenoxy>-2-propanols (VIa-r).Alkylation of IIIg-i and VIg,h and VIp with ethylchloroacetate gives the corresponding bisacetic acid esters Va-c and VIIa-c respectively.Some of the tested compounds exhibit in vitro growth inhibitory activity against Curvularia ovoidea and Rhizoctonia solani at concentrations of 25-50 μg/ml.
- Sangwan, Naresh K,Verma, Braham S,Dhindsa, Kuldip Singh
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p. 590 - 594
(2007/10/02)
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