Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

doi:10.1016/S1872-2067(12)60678-0

催化学报 ›› 2013, Vol. 34 ›› Issue (10): 1936-1944.DOI: 10.1016/S1872-2067(12)60678-0

Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

Ardeshir Khazaei^a, Mohammad Ali Zolfigol^a, Ahmad Reza Moosavi-Zare^b, Javad Afsar^a, Abdolkarim Zare^c, Vahid Khakyzadeh^a, Mohammad Hassan Beyzavi^d

a Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran;
b Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Iran;
c Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran;
d Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

收稿日期:2013-05-31 修回日期:2013-08-14 出版日期:2013-09-29 发布日期:2013-09-29
通讯作者: Ardeshir Khazaei,Mohammad Ali Zolfigol,Ahmad Reza Moosavi‐Zare

Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

Ardeshir Khazaei^a, Mohammad Ali Zolfigol^a, Ahmad Reza Moosavi-Zare^b, Javad Afsar^a, Abdolkarim Zare^c, Vahid Khakyzadeh^a, Mohammad Hassan Beyzavi^d

a Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran;
b Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Iran;
c Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran;
d Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

Received:2013-05-31 Revised:2013-08-14 Online:2013-09-29 Published:2013-09-29
Contact: Ardeshir Khazaei,Mohammad Ali Zolfigol,Ahmad Reza Moosavi‐Zare

摘要/Abstract

摘要：

Sulfonic acid functionalized pyridinium chloride [pyridine-SO₃H]Cl has been synthesized as a novel Brönsted acidic ionic liquid and characterized on the basis of its FT-IR, ¹H and ¹³C NMR, MS, thermogravimetry, and derivative thermogravimetry data. The material has also been used as a highly efficient, homogeneous, and reusable catalyst for the preparation of hexahydroquinolines according to the one-pot multi-component condensation of arylaldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters, and ammonium acetate under solvent-free conditions.

关键词: Brönsted acidic ionic liquid, Sulfonic acid functionalized pyridinium chloride [Pyridine-SO₃H]Cl, Hexahydroquinoline, Solvent-free synthesis

Abstract:

Key words: Brönsted acidic ionic liquid, Sulfonic acid functionalized pyridinium chloride [Pyridine-SO₃H]Cl, Hexahydroquinoline, Solvent-free synthesis

Ardeshir Khazaei, Mohammad Ali Zolfigol, Ahmad Reza Moosavi-Zare, Javad Afsar, Abdolkarim Zare, Vahid Khakyzadeh, Mohammad Hassan Beyzavi. Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst[J]. 催化学报, 2013, 34(10): 1936-1944.

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Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

Synthesis of hexahydroquinolines using the new ionic liquid sulfonic acid functionalized pyridinium chloride as a catalyst

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