Catalytic application of recyclable silica-supported bismuth(III) chloride in the benzo[N,N]-heterocyclic condensation
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Aghapoor, Kioumars
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Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, IranChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Aghapoor, Kioumars
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Mohsenzadeh, Farshid
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Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, IranChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Mohsenzadeh, Farshid
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Shakeri, Atena
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Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, IranChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Shakeri, Atena
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Darabi, Hossein Reza
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Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, IranChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Darabi, Hossein Reza
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Ghassemzadeh, Mitra
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Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, IranChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Ghassemzadeh, Mitra
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Neumueller, Bernhard
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Univ Marburg, Fachbereich Chem, D-35032 Marburg, GermanyChem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Neumueller, Bernhard
[2
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[1] Chem & Chem Engn Res Ctr Iran, Nano & Organ Synth Lab, Tehran 1496813151, Iran
Silica-supported bismuth(III) chloride (BiCl3/SiO2) has been successfully employed in the condensation of 1,2-dicarbonyls with a variety of arene-1,2-diamines bearing either electron withdrawing or donating functional groups. The catalyzed reaction proceeded smoothly under ambient temperature in methanol to give the corresponding quinoxaline and pyrido[2,3-b]pyrazine compounds in good to excellent yields. The catalyst exhibited remarkable reusable activity and higher catalytic performance than homogeneous BiCl3. A plausible mechanism for the catalytic action of BiCl3/SiO2 has been introduced. Moreover, the crystal structure of the prepared unsymmetrical benzo[N,N]-heterocycles has been determined by single crystal X-ray diffraction. (C) 2013 Elsevier B.V. All rights reserved.