An approach to the synthesis and characterization of HMS/Pr-Rh-Zr as efficient catalyst for synthesis of tetrahydrobenzo[b]pyran and 1,4-dihydropyrano[2,3-c]pyrazole derivatives

被引：16

作者：

Abdolahi, Sahar ^{[1
]}

Hajjami, Maryam ^{[2
]}

Gholamian, Fatemeh ^{[1
]}

机构：

[1] Ilam Univ, Fac Sci, Dept Chem, POB 69315516, Ilam, Iran

[2] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan 6517838683, Hamadan, Iran

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2021年 / 47卷 / 05期

关键词：

Mesoporous catalyst; Hexagonal mesoporous silica; HMS/pr-rh-zr; Tetrahydrobenzo[b]pyran; 1,4-dihydropyrano[2,3-c]pyrazole;

D O I：

10.1007/s11164-021-04411-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The aim of present investigation is the synthesis of mesoporous catalyst based on hexagonal mesoporous silica. HMS support has exceptional properties such as easy synthesis, high surface area, large pore volume and wormhole pores. These distinctive characteristics beseem use of it as a support for synthesis of heterogeneous catalyst. With functionalization of HMS and immobilization of Zr-rhodanine complex into functionalized HMS, HMS/Pr-Rh-Zr was obtained. New synthesized catalyst (HMS/Pr-Rh-Zr) characterized by FT-IR, XRD, TGA, SEM, EDX, adsorption-desorption of nitrogen at 77 K and ICP techniques. These techniques confirmed that the heterogeneous catalyst of HMS/Pr-Rh-Zr was successfully synthesized. Also the catalytic activity of HMS/Pr-Rh-Zr is investigated for the synthesis of tetrahydrobenzo[b]pyran derivatives from reaction between aldehyde, malononitrile, dimedone in PEG at 80 degrees C and synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives from reaction between aldehyde, ethyl acetoacetate, malononitrile and hydrazine hydrate in H2O:EtOH at 35 degrees C. These results confirmed the HMS/Pr-Rh-Zr exhibited good catalytic performance. Furthermore, the synthesized heterogeneous catalyst could be recovered after the reaction and reused several times without any noticeable loss in activity. Also zirconium leaching of HMS/Pr-Rh-Zr was studied whereupon metal leaching of the catalyst was very low. [GRAPHICS] .

引用

页码：1883 / 1904

页数：22

共 46 条

[1] Green and efficient synthesis of pyranopyrazoles using [bmim][OH-] as an ionic liquid catalyst in water under microwave irradiation and investigation of their antioxidant activity [J].

Aliabadi, Roghayeh Sharifi ;

Mahmoodi, Nosrat O. .

RSC ADVANCES, 2016, 6 (89) :85877-85884

[2] Fe3O4-supported N-pyridin-4-amine-grafted graphene oxide as efficient and magnetically separable novel nanocatalyst for green synthesis of 4H-chromenes and dihydropyrano[2,3-c]pyrazole derivatives in water [J].

Azarifar, Davood ;

Khaleghi-Abbasabadi, Masoud .

RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (02) :199-222

[3] Sulfonic acid-functionalized magnetic Fe3-xTixO4 nanoparticles: New recyclable heterogeneous catalyst for one-pot synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[2,3-c]pyrazole derivatives [J].

Azarifar, Davood ;

Abbasi, Younes .

SYNTHETIC COMMUNICATIONS, 2016, 46 (09) :745-758

[4] Mild and green synthesis of tetrahydrobenzopyran, pyranopyrimidinone and polyhydroquinoline derivatives and DFT study on product structures [J].

Bodaghifard, Mohammad Ali ;

Solimannejad, Mohammad ;

Asadbegi, Sajad ;

Dolatabadifarahani, Samira .

RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) :1165-1179

[5] 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

[6] Bovine serum albumin catalyzed one-pot, three-component synthesis of dihydropyrano[2,3-c] pyrazole derivatives in aqueous ethanol [J].

Dalal, Kiran S. ;

Tayade, Yogesh A. ;

Wagh, Yogesh B. ;

Trivedi, Darshak R. ;

Dalal, Dipak S. ;

Chaudhari, Bhushan L. .

RSC ADVANCES, 2016, 6 (18) :14868-14879

[7] Nano magnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica hybrid: Synthesis, characterization, and application as an efficient and reusable organic-inorganic hybrid silica with ionic liquid framework for one-pot synthesis of pyran annulated heterocyclic compounds in water [J].

Davarpanah, Jamal ;

Kiasat, Ali Reza ;

Noorizadeh, Siamak ;

Ghahremani, Mahboubeh .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 376 :78-89

[8] Schiff base-functionalized mesoporous silicas (MCM-41, HMS) as Pb(II) adsorbents [J].

Enache, Daniela F. ;

Vasile, Eugenia ;

Simonescu, Claudia Maria ;

Culita, Daniela ;

Vasile, Eugeniu ;

Oprea, Ovidiu ;

Pandele, Andreea Madalina ;

Razvan, Anca ;

Dumitru, Florina ;

Nechifor, Gheorghe .

RSC ADVANCES, 2018, 8 (01) :176-189

[9] A novel approach to the application of hexagonal mesoporous silica in solid-phase extraction of drugs [J].

Farjadian, Fatemeh ;

Azadi, Soha ;

Mohammadi-Samani, Soliman ;

Ashrafi, Hajar ;

Azadi, Amir .

HELIYON, 2018, 4 (11)

[10] Ag/TiO2 nano-thin films as robust heterogeneous catalyst for one-pot, multi-component synthesis of bis (pyrazol-5-ol) and dihydropyrano[2,3-c]pyrazole analogs [J].

Fatahpour, Maryam ;

Sadeh, Fatemeh Noori ;

Hazeri, Nourallah ;

Maghsoodlou, Malek Taher ;

Hadavi, Mohammad Saeed ;

Mahnaei, Sahar .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (08) :998-1006

← 1 2 3 4 5 →