Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal-Knorr pyrrole reaction under mild conditions

被引:18
作者
Azhdari, Asieh [1 ]
Azizi, Najmedin [1 ,2 ]
Sanaeishoar, Haleh [1 ]
Tahanpesar, Elham [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Ahvaz Branch, Ahvaz, Iran
[2] Chem & Chem Engn Res Ctr Iran, POB 14335-186, Tehran, Iran
来源
MONATSHEFTE FUR CHEMIE | 2021年 / 152卷 / 06期
关键词
Amidosulfonic acid; Nanocomposite; Pyrrole; Paal-Knorr reaction; g-C3N4; N-SUBSTITUTED PYRROLES; ONE-POT SYNTHESIS; SOLVENT-FREE SYNTHESIS; RECYCLABLE CATALYST; HIGHLY EFFICIENT; DEHYDRATIVE FORMATION; IONIC LIQUIDS; CHLORIDE; G-C3N4; DERIVATIVES;
D O I
10.1007/s00706-021-02771-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel heterogeneous acidic catalyst was prepared by in situ immobilization of amidosulfonic acid (NH2SO3H) on graphitic carbon nitride (g-C3N4) under hydrothermal conditions. The textural morphology of NH2SO3H/g-C3N4 nanocomposite was characterized via powder X-ray diffraction, FT-IR, TGA, EDX, and scanning electron microscopy. The spatial arrangement of the amidosulfonic acid on the surface of g-C3N4 leads to the construction of a unique solid acid structure, resulting in a substantial enhancement of catalytic activity toward a high efficient preparation of pyrroles by Paal-Knorr reaction. The reactions undergo completion readily with good to excellent yields, with simple purification in an environmentally friendly manner. The NH2SO3H/g-C3N4 nanocomposite can be readily recycled, and no noteworthy reduction in the catalytic activity detected after four runs. [GRAPHICS] .
引用
收藏
页码:625 / 634
页数:10
相关论文
共 53 条
[1]   Magnetically separable and recyclable g-C3N4 nanocomposite catalyzed one-pot synthesis of substituted imidazoles [J].
Ahooie, Tahereh Soleymani ;
Azizi, Najmedin ;
Yavari, Issa ;
Hashemi, Mohammad Mahmoudi .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (04) :855-862
[2]   Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media [J].
Azizi, Najmadin ;
Davoudpour, Anahita ;
Eskandari, Farshid ;
Batebi, Ehlham .
MONATSHEFTE FUR CHEMIE, 2013, 144 (03) :405-409
[3]   Greener construction of 4H-chromenes based dyes in deep eutectic solvent [J].
Azizi, Najmedin ;
Mariami, Mahboobe ;
Edrisi, Mahtab .
DYES AND PIGMENTS, 2014, 100 :215-221
[4]   Silicon Tetrachloride Catalyzed Aza-Michael Addition of Amines to Conjugated Alkenes under Solvent-Free Conditions [J].
Azizi, Najmedin ;
Baghi, Roya ;
Ghafuri, Hossein ;
Bolourtchian, Mohammad ;
Hashemi, Mohammad .
SYNLETT, 2010, (03) :379-382
[5]   Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water [J].
Azizi, Najmedin ;
Khajeh-Amiri, Alireza ;
Ghafuri, Hossein ;
Bolourtchian, Mohammad ;
Saidi, Mohammad Reza .
SYNLETT, 2009, (14) :2245-2248
[6]   Facile and One-Pot Access of 3,3-Bis(indol-3-yl)indolin-2-ones and 2,2-Bis(indol-3-yl)acenaphthylen-1(2H)-one Derivatives via an Eco-Friendly Pseudo-Multicomponent Reaction at Room Temperature Using Sulfamic Acid as an Organo-Catalyst [J].
Brahmachari, Goutam ;
Banerjee, Bubun .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (12) :2802-2812
[7]   Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst [J].
Brahmachari, Goutam ;
Banerjee, Bubun .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (03) :411-422
[8]   Graphitic carbon nitride and polymers: a mutual combination for advanced properties [J].
Cao, Qian ;
Kumru, Baris ;
Antonietti, Markus ;
Schmidt, Bernhard V. K. J. .
MATERIALS HORIZONS, 2020, 7 (03) :762-786
[9]   Catalytic application of room temperature ionic liquids:: [bmim][MeSO4] as a recyclable catalyst for synthesis of bis(indolyl) methanes. Ion-fishing by MALDI-TOF-TOF MS and MS/MS studies to probe the proposed mechanistic model of catalysis [J].
Chakraborti, Asit K. ;
Roy, Sudipta Raha ;
Kumar, Dinesh ;
Chopra, Pradeep .
GREEN CHEMISTRY, 2008, 10 (10) :1111-1118
[10]  
Chakraborti AK, 2007, GREEN CHEM, V9, P1335, DOI 10.1039/b710414f