Green synthesis of novel pyrano[2,3-c]pyrazole-5-carbonitrile analogues by using Fe5(PW10V2O40)3 nanocatalyst through a one-pot Knoevenagel condensation and Michael addition mechanism

被引：8

作者：

V. Subrahmanyam, Chittala ^{[1
]}

Rao, Battula Sreenivasa ^{[1
]}

Muralidhar, Pamerla ^{[1
]}

Rao, Lakinani Vaikunta ^{[1
]}

Gumbi, Bhekumuzi ^{[2
]}

Maddila, Suresh ^{[1
,2
]}

机构：

[1] GITAM Univ, GITAM Sch Sci, Dept Chem, Visakhapatnam, Andhra Pradesh, India

[2] Univ KwaZulu Natal, Sch Chem & Phys, Westville Campus,Chiltern Hills, ZA-4000 Durban, South Africa

来源：

INORGANIC CHEMISTRY COMMUNICATIONS | 2024年 / 159卷

关键词：

Environmental-benign; Green synthesis; Hetero-poly-acid; Multi-component reaction; One -pot synthesis; Recyclable; HETEROGENEOUS ACID CATALYSIS; MULTICOMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; REUSABLE CATALYST; HETEROPOLY ACIDS; SOLVENT;

D O I：

10.1016/j.inoche.2023.111906

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A swift and green one-pot method was improved for the preparation of new pyranopyrazole analogues using iron-doped heteropoly acid [(Fe-5(PW10V2O40)(3)] (FePWV) as an efficient catalyst at room temperature and ethanol as the solvent. The one-pot, multi-component reaction combining substituted aldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate produces remarkable yields (varying from 88 % to 98 %) for this highly selective technique. Using P-XRD, TGA, BET, FT-IR, TEM, and SEM studies, the synthesized FePWV catalyst was fully characterized. Several spectroscopic methods, including H-1 NMR,N- 15 NMR, C-13 NMR, and HRMS, were used to confirm the target molecules' structural information. This environmentally benign method also has other benefits, such as operational simplicity, a stable catalyst with great reusability (up to 7 times), quick reaction times (<20 min), and the absence of chromatographic separations. The proposed method is sustainable and affordable as a result of these properties taken together.

引用

页数：7

共 38 条

[1] A green and one-pot synthesis of a library of 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using thiourea dioxide (TUD) as an efficient and reusable organocatalyst
Rajesh H. Vekariya
Kinjal D. Patel
Hitesh D. Patel
Research on Chemical Intermediates, 2016, 42 : 4683 - 4696
[2] A green and one-pot synthesis of a library of 1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using thiourea dioxide (TUD) as an efficient and reusable organocatalyst
Vekariya, Rajesh H.
Patel, Kinjal D.
Patel, Hitesh D.
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (05) : 4683 - 4696
[3] A green and one-pot synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using CoCeO2 nanoparticles as an efficient, reusable and heterogeneous catalyst
Shaikh, Shaheen A.
Kamble, Vishal S.
Zemase, Rohan K.
Patil, Sanjay K.
Aghav, Balasaheb D.
RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (12) : 5255 - 5272
[4] A green and one-pot synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using CoCeO2 nanoparticles as an efficient, reusable and heterogeneous catalyst
Shaheen A. Shaikh
Vishal S. Kamble
Rohan K. Zemase
Sanjay K. Patil
Balasaheb D. Aghav
Research on Chemical Intermediates, 2023, 49 : 5255 - 5272
[5] One-pot multicomponent synthesis in aqueous medium of 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and derivatives using a green and reusable nano-SiO2 catalyst from agricultural waste
Patel, Khushbu G.
Misra, Nirendra M.
Vekariya, Rajesh H.
Shettigar, Rakshith R.
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (01) : 289 - 304
[6] One-pot multicomponent synthesis in aqueous medium of 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile and derivatives using a green and reusable nano-SiO2 catalyst from agricultural waste
Khushbu G. Patel
Nirendra M. Misra
Rajesh H. Vekariya
Rakshith R. Shettigar
Research on Chemical Intermediates, 2018, 44 : 289 - 304
[7] A novel and efficient one-pot synthesis of furo[3′,4′:5,6]pyrido[2,3-c]pyrazole derivatives using organocatalysts
Shi, Chun-Ling
Shi, Da-Qing
Kim, Sung Hong
Huang, Zhi-Bin
Ji, Shun-Jun
Ji, Min
TETRAHEDRON, 2008, 64 (10) : 2425 - 2432
[8] Nano silica extracted from horsetail plant as a natural silica support for the synthesis of H3PW12O40 immobilized on aminated magnetic nanoparticles (Fe3O4@SiO2-EP-NH-HPA): a novel and efficient heterogeneous nanocatalyst for the green one-pot synthesis of pyrano[2,3-c]pyrazole derivatives
Mohtasham, Nina
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RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (06) : 3037 - 3066
[9] Nano silica extracted from horsetail plant as a natural silica support for the synthesis of H3PW12O40 immobilized on aminated magnetic nanoparticles (Fe3O4@SiO2-EP-NH-HPA): a novel and efficient heterogeneous nanocatalyst for the green one-pot synthesis of pyrano[2,3-c]pyrazole derivatives
Nina Hosseini Mohtasham
Mostafa Gholizadeh
Research on Chemical Intermediates, 2020, 46 : 3037 - 3066
[10] An efficient protocol for the one-pot four-component synthesis of 6-amino-1, 4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using starch solution as a reaction media
Vekariya, Rajesh H.
Patel, Kinjal D.
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INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2018, 57 (04): : 576 - 582

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