Microwave-Assisted Synthesis as an Efficient Method to Enhance the Catalytic Activity of Zr-Based Metal Organic Framework UiO-66 in a Heterocyclization Reaction

被引:45
作者
Linh Ho Thuy Nguyen [1 ,2 ]
Trang Thi Thu Nguyen [1 ,2 ]
Thi Dang, Y. [1 ]
Phuong Hoang Tran [2 ]
Tan Le Hoang Doan [1 ,2 ]
机构
[1] Vietnam Natl Univ Ho Chi Minh City VNU HCM, Ctr Innovat Mat & Architectures INOMAR, Ho Chi Minh City 721337, Vietnam
[2] Vietnam Natl Univ Ho Chi Minh City, Dept Organ Chem, Fac Chem, Univ Sci, Ho Chi Minh City 721337, Vietnam
关键词
metal-organic frameworks; heterocycles; ring-closure reaction; quinazolinones; heterogeneous catalysis; microwave chemistry; DEFECTS; QUINAZOLINONES; OPTIMIZATION; MOF;
D O I
10.1002/ajoc.201900556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Zr-based metal-organic frameworks have been considered promising heterogeneous catalysts in various reactions. It has been proven that the defect sites in these frameworks, which result from deficiency of linkers, could act as the reaction active sites. In this work, microwave irradiation was used for rapid synthesis and increasing defects on Zr-6 clusters of metal-organic framework UiO-66. Powder X-ray diffraction, thermal gravimetric analysis, and N-2 sorption isotherms were performed to characterize and calculate the defect number in the framework. UiO-66 prepared by microwave method for a few minutes could reach 1.8 missing linkers per cluster. The material with acetic acid as a co-catalyst showed highly heterogeneous catalytic activity in the solvent-free heterocyclization of 2,2-disubstituted 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and ketones/aldehydes. The synthetic scheme consisted of zirconium cluster catalysed carbonyl group of anthranilamide to achieve the C-N propitious combination and succeeding ring closure process.
引用
收藏
页码:2276 / 2281
页数:6
相关论文
共 50 条
[1]   An Ullmann N-arylation/2-amidation cascade by self-relay copper catalysis: one-pot synthesis of indolo[1,2-a]quinazolinones [J].
Abe, Takumi ;
Takahashi, Yuka ;
Matsubara, Yuki ;
Yamada, Koji .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11) :2124-2127
[2]   Zr-based metal-organic frameworks: design, synthesis, structure, and applications [J].
Bai, Yan ;
Dou, Yibo ;
Xie, Lin-Hua ;
Rutledge, William ;
Li, Jian-Rong ;
Zhou, Hong-Cai .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2327-2367
[3]   A new zirconium inorganic building brick forming metal organic frameworks with exceptional stability [J].
Cavka, Jasmina Hafizovic ;
Jakobsen, Soren ;
Olsbye, Unni ;
Guillou, Nathalie ;
Lamberti, Carlo ;
Bordiga, Silvia ;
Lillerud, Karl Petter .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (42) :13850-13851
[4]   Metal-organic framework-derived porous materials for catalysis [J].
Chen, Yu-Zhen ;
Zhang, Rui ;
Jiao, Long ;
Jiang, Hai-Long .
COORDINATION CHEMISTRY REVIEWS, 2018, 362 :1-23
[5]   Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2•12H2O as a reusable catalyst in water and ethanol [J].
Dabiri, M ;
Salehi, P ;
Otokesh, S ;
Baghbanzadeh, M ;
Kozehgary, G ;
Mohammadi, AA .
TETRAHEDRON LETTERS, 2005, 46 (36) :6123-6126
[6]  
Das S, 2017, EUR J ORG CHEM 0908, V2017, P4955
[7]   Engineering UiO-66 Metal Organic Framework for Heterogeneous Catalysis [J].
Dhakshinamoorthy, Amarajothi ;
Santiago-Portillo, Andrea ;
Asiri, Abdullah M. ;
Garcia, Hermenegildo .
CHEMCATCHEM, 2019, 11 (03) :899-923
[8]   An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation [J].
Doan, Tan L. H. ;
Dao, Thong Q. ;
Tran, Hai N. ;
Tran, Phuong H. ;
Le, Thach N. .
DALTON TRANSACTIONS, 2016, 45 (18) :7875-7880
[9]   Tailoring the Optical Absorption of Water-Stable ZrIV- and HfIV- Based Metal-Organic Framework Photocatalysts [J].
Doan, Tan L. H. ;
Nguyen, Ha L. ;
Pham, Hung Q. ;
Nguyen-Nguyen Pham-Tran ;
Le, Thach N. ;
Cordova, Kyle E. .
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (12) :2659-2667
[10]   Synthesis of 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and ketones over H zeolite in aqueous media [J].
Gajula, Krishna Sai ;
Mameda, Naresh ;
Kodumuri, Srujana ;
Chevella, Durgaiah ;
Banothu, Rammurthy ;
Amrutham, Vasu ;
Kutepov, Boris Ivanovich ;
Nama, Narender .
SYNTHETIC COMMUNICATIONS, 2018, 48 (22) :2866-2876