Crystalline salicylic acid as an efficient catalyst for ultrafast Paal-Knorr pyrrole synthesis under microwave induction

被引:9
作者
Aghapoor, Kioumars [1 ]
Mohsenzadeh, Farshid [1 ]
Darabi, Hossein Reza [1 ]
Sayahi, Hani [1 ]
机构
[1] Chem & Chem Engn Res Ctr Iran, Appl Chem Synth Lab, Pajoohesh Blvd,Km 17, Tehran 1496813151, Iran
基金
英国科研创新办公室;
关键词
Salicylic acid and microwaves; Organocatalysis; Paal-Knorr reaction; 2,5-dimethylpyrrole; SOLVENT-FREE; SUBSTITUTED PYRROLES; ASSISTED SYNTHESIS; POTENT INHIBITORS; MOLECULAR DOCKING; GREEN; DERIVATIVES; ORGANOCATALYSIS; FEATURES; DESIGN;
D O I
10.1007/s12039-021-01891-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, the viability of a wide range of crystalline aromatic and aliphatic carboxylic acids as organocatalysts has been investigated for solvent-free Paal-Knorr pyrrole synthesis under microwave activation. Among these potential catalysts, crystalline salicylic acid proved to be a remarkable catalyst because its efficiency remained high even under low microwave power irradiation or a shorter reaction time for the model reaction. The outstanding catalytic activity of salicylic acid allowed the Paal-Knorr cyclocondensation with a turnover frequency up to 1472 h(-1) which is unique in the context of a metal-free homogeneous catalysis. The attractive feature of this organocatalyst is its assistance in ultrafast pyrrole synthesis with no risk of metal contamination.
引用
收藏
页数:8
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共 56 条
[1]   Microwave-induced calcium(II) chloride-catalyzed Paal-Knorr pyrrole synthesis: a safe, expeditious, and sustainable protocol [J].
Aghapoor, Kioumars ;
Mohsenzadeh, Farshid ;
Darabi, Hossein Reza ;
Rastgar, Saeed .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (07) :4063-4072
[2]   L-Tryptophan-catalyzed Paal-Knorr pyrrole cyclocondensation: an efficient, clean and recyclable organocatalyst [J].
Aghapoor, Kioumars ;
Mohsenzadeh, Farshid ;
Darabi, Hossein Reza ;
Sayahi, Hani ;
Balavar, Yadollah .
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) :407-415
[3]   Catalytic activity of the nanoporous MCM-41 surface for the Paal-Knorr pyrrole cyclocondensation [J].
Aghapoor, Kioumars ;
Amini, Mostafa M. ;
Jadidi, Khosrow ;
Mohsenzadeh, Farshid ;
Darabi, Hossein Reza .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2015, 70 (07) :475-481
[4]   Silica-supported bismuth(III) chloride as a new recyclable heterogeneous catalyst for the Paal-Knorr pyrrole synthesis [J].
Aghapoor, Kioumars ;
Ebadi-Nia, Leila ;
Mohsenzadeh, Farshid ;
Morad, Mina Mohebi ;
Balavar, Yadollah ;
Darabi, Hossein Reza .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 708 :25-30
[5]   Pyrrole: An insight into recent pharmacological advances with structure activity relationship [J].
Ahmad, Shujauddin ;
Alam, Ozair ;
Naim, Mohd. Javed ;
Shaquiquzzaman, Mohammad ;
Alam, M. Mumtaz ;
Iqbal, Muzaffar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 157 :527-561
[6]   Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities [J].
Akhtar, Jawaid ;
Khan, Ahsan Ahmed ;
Ali, Zulphikar ;
Haider, Rafi ;
Yar, M. Shahar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 :143-189
[7]   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
[8]   Paal-Knorr synthesis of pyrroles: from conventional to green synthesis [J].
Balakrishna, Avula ;
Aguiar, Antonio ;
Sobral, Pedro J. M. ;
Wani, Mohmmad Younus ;
Almeida e Silva, Joana ;
Sobral, Abilio J. F. N. .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2019, 61 (01) :84-110
[9]   Simple synthesis of substituted pyrroles [J].
Banik, BK ;
Samajdar, S ;
Banik, I .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) :213-216
[10]   New derivatives of BM212: A class of antimycobacterial compounds based on the pyrrole ring as a scaffold [J].
Biava, M. ;
Porretta, G. C. ;
Manetti, F. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (01) :65-78