Pyridine-2-carboxylic acid as an effectual catalyst for rapid multi-component synthesis of pyrazolo[3,4-b]quinolinones

被引：34

作者：

Sharma, Mayank G. ^{[1
]}

Vala, Ruturajsinh M. ^{[1
]}

Patel, Hitendra M. ^{[1
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Univ Campus, Vallabh Vidyanagar 388120, Gujarat, India

来源：

RSC ADVANCES | 2020年 / 10卷 / 58期

关键词：

ONE-POT; REGIOSELECTIVE SYNTHESIS; MANNICH PRODUCTS; FACILE SYNTHESIS; DERIVATIVES; EFFICIENT; GREEN; WATER;

D O I：

10.1039/d0ra06738e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Green synthesis of pyrazolo[3,4-b]quinolinones was designed using bioproduct pyridine-2-carboxylic acid (P2CA) as a green and efficient catalyst. The multi-component reaction of aldehydes, 1,3-cyclodiones and 5-amino-1-phenyl-pyrazoles regioselectively produced pyrazolo[3,4-b]quinolinones in excellent yield (84-98%). Recyclization of the catalyst was also investigated. The electronic effect of the various substituents in aromatic rings indicated that the reaction proceeded through the carbocation intermediate. This newly designed protocol very quickly constructed products conventionally under milder conditions.

引用

页码：35499 / 35504

页数：6

共 38 条

[1] Antileishmanial Activity of Pyrazolopyridine Derivatives and Their Potential as an Adjunct Therapy with Miltefosine [J].

Anand, Devireddy ;

Yadav, Pawan Kumar ;

Patel, Om P. S. ;

Parmar, Naveen ;

Maurya, Rahul K. ;

Vishwakarma, Preeti ;

Raju, Kanumuri S. R. ;

Taneja, Isha ;

Wahajuddin, M. ;

Kar, Susanta ;

Yadav, Prem P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (03) :1041-1059

[2] New pyrazolyl-dibenzo[b,e][1,4]diazepinones: room temperature one-pot synthesis and biological evaluation [J].

Brahmbhatt, Gaurangkumar C. ;

Sutariya, Tushar R. ;

Atara, Hiralben D. ;

Parmar, Narsidas J. ;

Gupta, Vivek K. ;

Lagunes, Irene ;

Padron, Jose M. ;

Murumkar, Prashant R. ;

Yadav, Mange Ram .

MOLECULAR DIVERSITY, 2020, 24 (02) :355-377

[3] Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes [J].

Chebanov, Valentin A. ;

Saraev, Vyacheslav E. ;

Desenko, Sergey M. ;

Chernenko, Vitaliy N. ;

Knyazeva, Irina V. ;

Groth, Ulrich ;

Glasnov, Tortia N. ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5110-5118

[4] One-pot, multicomponent route to pyrazoloquinolizinones [J].

Chebanov, Valentin A. ;

Saraev, Vyacheslav E. ;

Desenko, Sergey M. ;

Chemenko, Vitaliy N. ;

Shishkina, Svetlana V. ;

Shishkin, Oleg V. ;

Kobzar, Kiril M. ;

Kappe, C. Oliver .

ORGANIC LETTERS, 2007, 9 (09) :1691-1694

[5] 4-Aminoindoles as 1,4-bisnucleophiles for diversity-oriented synthesis of tricyclic indoles bearing 3,4-fused seven-membered rings [J].

Chen, Shaomin ;

Ravichandiran, Palanisamy ;

El-Harairy, Ahmed ;

Queneau, Yves ;

Li, Minghao ;

Gu, Yanlong .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (24) :5982-5989

[6] Reactive Extraction of Picolinic Acid Using Tri-n-octylamine Dissolved in Different Diluents: Effect of Solvent Polarity [J].

Datta, Dipaloy ;

Kumar, Sushil .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2015, 60 (09) :2709-2716

[7]

Drees B., 2007, US Pat, Patent No. [US 2007/0010548 A1, 20070010548]

[8]

Drizin I., 2003, US Pat, Patent No. [US 6538004 B2, 6538004]

[9] Novel Non-toxic and Non-hazardous Solvent Systems for the Chemistry of Indoles: Use of a Sulfone-containing Bronsted Acid Ionic Liquid Catalyst in Butyl Acetate [J].

El-Harairy, Ahmed ;

Yiliqi ;

Yue, Meie ;

Fan, Weigang ;

Popowycz, Florence ;

Queneau, Yves ;

Li, Minghao ;

Gu, Yanlong .

CHEMCATCHEM, 2019, 11 (17) :4403-4410

[10] Efficient Passivation with Lead Pyridine-2-Carboxylic for High-Performance and Stable Perovskite Solar Cells [J].

Fu, Sheng ;

Li, Xiaodong ;

Wan, Li ;

Wu, Yulei ;

Zhang, Wenxiao ;

Wang, Yueming ;

Bao, Qinye ;

Fang, Junfeng .

ADVANCED ENERGY MATERIALS, 2019, 9 (35)

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