Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
Submit an article Journal homepage
4,900
Views
52
CrossRef citations to date
0
Altmetric
Original Articles

Room-Temperature Synthesis of Pyrazoles, Diazepines, β-Enaminones, and β-Enamino Esters Using Silica-Supported Sulfuric Acid as a Reusable Catalyst Under Solvent-Free Conditions

Xiang Chen Department of Chemistry, Zhejiang University, Hangzhou, China
,
Jin She Department of Chemistry, Zhejiang University, Hangzhou, China
,
Zhi-Cai Shang Department of Chemistry, Zhejiang University, Hangzhou, ChinaCorrespondence[email protected]
,
Jun Wu Department of Chemistry, Zhejiang University, Hangzhou, China
&
Peizhi Zhang School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou, China
Pages 947-957 | Received 06 Jul 2008, Published online: 25 Feb 2009

Citations (52)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (4)

Cherupally Dayakar, Dondra Jyothi, Pathi Suman & Bhimapaka China Raju. (2015) Condensation of Ortho-phenylenediamines and Phenylhydrazines with Ethyl 4-Chloro-3-oxobutanoate: A Facile Approach for the Synthesis of Substituted 1H-Benzimidazoles, Pyrazolones, and Pyrazoles. Synthetic Communications 45:14, pages 1642-1651.
Read now
HemantS. Chandak, NitinP. Lad & DipaliS. Dange. (2012) Greener and facile aqueous synthesis of pyrazoles using Amberlyst-70 as a recyclable catalyst. Green Chemistry Letters and Reviews 5:2, pages 135-138.
Read now
MohanR. Shetty & ShriniwasD. Samant. (2012) Sulfamic Acid (H2NSO3H): A Low-Cost, Mild, and Efficient Catalyst for the Synthesis of Substituted N-Phenylpyrazoles Under Solvent-Free Conditions. Synthetic Communications 42:10, pages 1411-1418.
Read now
Xing-Hai Liu, Cheng-Xia Tan & Jian-Quan Weng. (2011) Synthesis, Dimeric Crystal Structure, and Fungicidal Activity of 1-(4-Methylphenyl)-2-(5-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)ethanone. Phosphorus, Sulfur, and Silicon and the Related Elements 186:3, pages 558-564.
Read now

Articles from other publishers (48)

Sushma Yadav, Arti Jain & Priti Malhotra. (2024) Nanocatalyst driven synthesis of β-enaminones: A novel step towards the development of pharmaceutical precursors. Journal of the Indian Chemical Society 101:2, pages 101119.
Crossref
Kamal Das, Barnali Das, Bhaswati Paul, Ramalingam Natarajan & Swapan Majumdar. (2023) H-Bond Driven Solvent-Free Rapid Access of β-enamino Esters/Ketones using 230-400 Mesh Silica Gel as a Catalyst. Silicon 16:2, pages 967-977.
Crossref
Sushma Singh, Sidhant Yadav, Minakshi Minakshi & Rashmi Pundeer. (2023) Green Synthesis of Pyrazoles: Recent Developments in Aqueous Methods. SynOpen 07:03, pages 297-312.
Crossref
Sagar R. Kande. (2022) Succinimide-N-sulfonic Acid Catalyzed One Pot, Efficient Synthesis of Substituted Pyrazoles. Oriental Journal Of Chemistry 38:4, pages 1059-1063.
Crossref
Mengyuan Cheng, Yufeng Liu, Weixin Du, Jingwen Shi, Junhua Li, Haiying Wang, Ke Li, Guoping Yang & Dongdi Zhang. (2022) Two Dawson-type U(VI)-containing selenotungstates with sandwich structure and its high‐efficiency catalysis for pyrazoles. Chinese Chemical Letters 33:8, pages 3899-3902.
Crossref
Aekkaphon Mokkarat, Senee Kruanetr & Uthai Sakee. (2022) Facial preparation of trifluoroacetic acid-immobilized amino-functionalized silica magnetite nano-catalysts as a highly efficient and reusable for synthesis of β-enaminones. Journal of Molecular Structure 1259, pages 132745.
Crossref
Jie Zhou, Tao Yu, Ke Li, Kai Zeng, Guo-Ping Yang & Chang-Wen Hu. (2022) Two U(VI)-Containing Silicotungstates with Sandwich Structures: Lewis Acid–Base Synergistic Catalyzed Synthesis of Benzodiazepines and Pyrazoles. Inorganic Chemistry 61:7, pages 3050-3057.
Crossref
Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang & Jijiang Wang. (2022) Construction of Substituted N -Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process . Chinese Journal of Organic Chemistry 42:6, pages 1843.
Crossref
Andrew N. Boa & Martin J. McPhillie. 2022. Comprehensive Heterocyclic Chemistry IV. Comprehensive Heterocyclic Chemistry IV 243 268 .
Leimajam Vartima Chanu & Okram Mukherjee Singh. (2021) Recent progress in the synthesis of azoles and related five‐membered ring heterocycles using silica‐supported heterogeneous catalysts. Journal of Heterocyclic Chemistry 58:12, pages 2207-2225.
Crossref
Atif Mustafa, Shaheen Siddiqui, Mohd Umar Khan, Abdulaziz Abdullah Qasem Ali & Zeba N. Siddiqui. (2021) Recent Advances in Synthesis of Pyrazole Derivatives using Functionalized Catalysts Immobilized on Silica. ChemistrySelect 6:33, pages 8611-8629.
Crossref
Divya Sree Uppalapati, Rama Sekhara Reddy Dachuru & Satya Veni Sunkara. (2021) Silica sulfuric acid mediated synthesis of naphtho[2,1‐ b ]furan derivatives and development of  one‐pot  multicomponent synthesis of substituted pyrazole derivatives . Journal of Heterocyclic Chemistry 58:8, pages 1695-1699.
Crossref
Anjana Delpe-Acharige, Man Zhang, Kayla Eschliman, Alex Dalecki, Obdulia Covarrubias-Zambrano, Azriel Minjarez-Almeida, Tejaswi Shrestha, Tanji Lewis, Fatimah Al-Ibrahim, Sophia Leonard, Riana Roberts, Anteneh Tebeje, Aruni P. Malalasekera, Hongwang Wang, Madumali Kalubowilage, Frank Wolschendorf, Olaf Kutsch & Stefan H. Bossmann. (2021) Pyrazolyl Thioureas and Carbothioamides with an NNSN Motif against MSSA and MRSA. ACS Omega 6:9, pages 6088-6099.
Crossref
J. D. Bhirud, G. R. Gupta & H. P. Narkhede. (2020) Oxidative Cyclization of Chalcones in the Presence of Sulfamic Acid as Catalyst. Synthesis, Biological Activity, and Thermal Properties of 1,3,5-Trisubstituted Pyrazoles. Russian Journal of Organic Chemistry 56:10, pages 1815-1822.
Crossref
Adelew Estifanos Filkale & Chandni Pathak. (2020) Dinuclear cobalt complexes supported by biphenol and binaphthol-derived bis(salicylaldimine) ligands: synthesis, characterization and catalytic application in β-enaminone synthesis from 1,3-dicarbonyl compounds and aliphatic amines. New Journal of Chemistry 44:35, pages 15109-15121.
Crossref
Ezzat Khan, Muhammad Khalid, Zarif Gul, Adnan Shahzad, Muhammad Nawaz Tahir, Hafiz Muhammad Asif, Sumreen Asim & Ataualpa Albert Carmo Braga. (2020) Molecular structure of 1,4-bis(substituted-carbonyl)benzene: A combined experimental and theoretical approach. Journal of Molecular Structure 1205, pages 127633.
Crossref
Qiaohe Zhang, Biao Hu, Yuxuan Zhao, Siyun Zhao, Yanqin Wang, Biao Zhang, Shengjiao Yan & Fuchao Yu. (2020) Synthesis of N ‐Sulfonyl Pyrazoles Through Cyclization Reactions of Sulfonyl Hydrazines with Enaminones Promoted by p ‐TSA . European Journal of Organic Chemistry 2020:9, pages 1154-1159.
Crossref
Pargat Singh & Mahendra Nath. (2019) A Concise Account on Eco-friendly Synthetic Strategies for Pyrazole Heterocycles. Current Green Chemistry 6:3, pages 198-209.
Crossref
Sabrina A. Almeida Batista, Fábio Vandresen, Hugo Falzirolli, Elizandra Britta, Diogo N. de Oliveira, Rodrigo R. Catharino, Mateus A. Gonçalves, Teodorico C. Ramalho, Felipe A. La Porta, Celso V. Nakamura & Cleuza C. da Silva. (2019) Synthesis and comparison of antileishmanial and cytotoxic activities of S-(−)-limonene benzaldehyde thiosemicarbazones with their R-(+)-analogues. Journal of Molecular Structure 1179, pages 252-262.
Crossref
Seyyed Rasul Mousavi, Hassan Sereshti, Hamid Rashidi Nodeh & Alireza Foroumadi. (2018) A novel and reusable magnetic nanocatalyst developed based on graphene oxide incorporated strontium nanoparticles for the facial synthesis of β‐enamino ketones under solvent‐free conditions. Applied Organometallic Chemistry 33:1.
Crossref
Thalita F.B. de Aquino, Jessica P. Seidel, Daniela H. de Oliveira, José Edmilson R. do Nascimento, Diego Alves, Gelson Perin, Eder J. Lenardão, Ricardo F. Schumacher & Raquel G. Jacob. (2018) Copper-catalyzed synthesis of 1,3,5-triaryl-4-(organylselanyl)-1H-pyrazoles by one-pot multicomponent reactions. Tetrahedron Letters 59:46, pages 4090-4095.
Crossref
Se Hun Kwak, Nurbey Gulia & Olafs Daugulis. (2018) Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C–H Bond Functionalization Methodology. The Journal of Organic Chemistry 83:10, pages 5844-5850.
Crossref
Hashem Sharghi, Jasem Aboonajmi, Mozhdeh Mozaffari, Mohammad Mahdi Doroodmand & Mahdi Aberi. (2017) Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds. Applied Organometallic Chemistry 32:3.
Crossref
John S. Maass, Randall K. Wilharm, Rudy L. Luck & Matthias Zeller. (2018) Photoluminescent properties of three lanthanide compounds of formulae LnCl3(diphenyl((5-phenyl-1H-pyrazol-3-yl)methyl)phosphine oxide)2, Ln = Sm, Eu and Tb: X-ray structural, emission and vibrational spectroscopies, DFT and thermogravimetric studies. Inorganica Chimica Acta 471, pages 481-492.
Crossref
Bhaskar Sarmah & Rajendra Srivastava. (2017) Octahedral MnO 2 Molecular Sieve-Decorated Meso -ZSM-5 Catalyst for Eco-Friendly Synthesis of Pyrazoles and Carbamates . Industrial & Engineering Chemistry Research 56:51, pages 15017-15029.
Crossref
Goutam Brahmachari. 2017. Catalyst-free Organic Synthesis. Catalyst-free Organic Synthesis 253 313 .
Carla I. Nieto, Rosa M. Claramunt, M. Carmen Torralba, M. Rosario Torres & Jose Elguero. (2017) Crystal structure of (1 Z ,4 Z )-2,4-dimethyl-3 H -benzo[ b ][1,4]diazepine . Acta Crystallographica Section E Crystallographic Communications 73:5, pages 647-650.
Crossref
Zhi-Hao Zhou, Cheng-Kun Li, Shao-Fang Zhou, Adedamola Shoberu & Jian-Ping Zou. (2017) Copper-catalyzed methylation of 1,3-diketones with tert-butyl peroxybenzoate. Tetrahedron 73:19, pages 2740-2746.
Crossref
Felipe Wodtke, Fernando R. Xavier, Samuel R. Mendes, Alfredo R.M. de Oliveira & Rogério A. Gariani. (2017) A simple protocol for the preparation of β-enamino ketones catalyzed by NbOPO4 under solvent free conditions. Tetrahedron Letters 58:3, pages 231-234.
Crossref
Colin H. McAteer, Ramiah Murugan & Yarlagadda V. Subba Rao. 2017. Heterocyclic Chemistry in the 21st Century - A Tribute to Alan Katritzky. Heterocyclic Chemistry in the 21st Century - A Tribute to Alan Katritzky 173 205 .
Ian J. Bakanas & Gustavo Moura‐Letts. (2016) Synthesis of Tetrasubstituted Pyrazoles from Substituted Hydrazines and β‐Keto Esters. European Journal of Organic Chemistry 2016:32, pages 5345-5349.
Crossref
Heshmatollah Alinezhad, Mahmood Tajbakhsh, Malihe Norouzi Sarkati & Mahboobe Zare. (2016) Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions. Monatshefte für Chemie - Chemical Monthly 147:9, pages 1591-1596.
Crossref
A. M. Maharramov, A. I. Ismiyev, M. A. Allahverdiyev, A. V. Maleev & K. A. Potekhin. (2016) Crystal structure of phenylhydrazine with diacetyl substituted ketol of the cyclohexane series. Journal of Structural Chemistry 57:4, pages 764-770.
Crossref
Daniela H. Oliveira, Thalita B. Aquino, José Edmilson R. Nascimento, Gelson Perin, Raquel G. Jacob & Diego Alves. (2015) Direct Synthesis of 4‐Organylselanylpyrazoles by Copper‐ Catalyzed One‐Pot Cyclocondensation and CH Bond Selenylation Reactions. Advanced Synthesis & Catalysis 357:18, pages 4041-4049.
Crossref
Ananda Mane, Prabha Salokhe, Pallavi More & Rajashri Salunkhe. (2015) An efficient practical chemo-enzymatic protocol for the synthesis of pyrazoles in aqueous medium at ambient temperature. Journal of Molecular Catalysis B: Enzymatic 121, pages 75-81.
Crossref
Samira Bahemmat, Bernhard Neumüller & Mitra Ghassemzadeh. (2015) One‐Pot Synthesis of an Oxalato‐Bridged Cu II Coordination Polymer Containing an In Situ Produced Pyrazole Moiety: A Precursor for the Preparation of CuO Nano­structures . European Journal of Inorganic Chemistry 2015:24, pages 4116-4124.
Crossref
Abdolhamid Bamoniri, Bi Bi Fatemeh Mirjalili & Naimeh Moshtael-Arani. (2014) Nano BF3·SiO2: A green heterogeneous solid acid for synthesis of formazan dyes under solvent-free condition. Journal of Molecular Catalysis A: Chemical 393, pages 272-278.
Crossref
Chengliang Feng, Shuguang Zhang, Jin Cai, Junqing Chen, Huayou Hu & Min Ji. (2019) Zinc Triflate Catalysed Synthesis of β-Enamino Ketones(Esters) under Solvent-Free Conditions. Journal of Chemical Research 37:10, pages 626-629.
Crossref
Jian Sun, Zhengping Dong, Ping Li, Fengwei Zhang, Shuoyun Wei, Zhiqiang Shi & Rong Li. (2013) Ag nanoparticles in hollow magnetic mesoporous spheres: A highly efficient and magnetically separable catalyst for synthesis of β-enaminones. Materials Chemistry and Physics 140:1, pages 1-6.
Crossref
Buchi Reddy Vaddula, Rajender S. Varma & John Leazer. (2013) Mixing with microwaves: solvent-free and catalyst-free synthesis of pyrazoles and diazepines. Tetrahedron Letters 54:12, pages 1538-1541.
Crossref
Liangguang Wang, Xiaoqiang Yu, Xiujuan Feng & Ming Bao. (2013) Synthesis of 3,5-Disubstituted Pyrazoles via Cope-Type Hydroamination of 1,3-Dialkynes. The Journal of Organic Chemistry 78:4, pages 1693-1698.
Crossref
James H. Clark, James W. Comerford & D. J. Macquarrie. 2013. Innovations in Green Chemistry and Green Engineering. Innovations in Green Chemistry and Green Engineering 37 80 .
Weibing Liu, Cui Chen & Qing Zhang. (2012) FeCl 3 -PTSA Co-Catalysed Highly Regio- and Stereo-Selective Synthesis of β-Functionalised Enamine Derivatives . Journal of Chemical Research 36:3, pages 175-177.
Crossref
James H. Clark, James W. Comerford & D. J. Macquarrie. 2019. Green Chemistry and Chemical Engineering. Green Chemistry and Chemical Engineering 51 81 .
James H. Clark, James W. Comerford & D. J. Macquarrie. 2012. Encyclopedia of Sustainability Science and Technology. Encyclopedia of Sustainability Science and Technology 4584 4614 .
Tyler J. Morin, Sarath Wanniarachchi, Chengeto Gwengo, Vitales Makura, Heidi M. Tatlock, Sergey V. Lindeman, Brian Bennett, Gary J. Long, Fernande Grandjean & James R. Gardinier. (2011) Pyrazolyl methyls prescribe the electronic properties of iron(ii) tetra(pyrazolyl)lutidine chloride complexes. Dalton Transactions 40:31, pages 8024.
Crossref
Ju‐Yan Liu, Gai‐E Cao, Wei Xu, Jie Cao & Wei‐Lu Wang. (2010) Ni(OAc) 2 : a highly efficient catalyst for the synthesis of enaminone and enamino ester derivatives under solvent‐free conditions . Applied Organometallic Chemistry 24:10, pages 685-691.
Crossref
Xiang Chen, Jin She, Zhi‐Cai Shang, Jun Wu & Peizhi Zhang. (2009) ChemInform Abstract: Room‐Temperature Synthesis of Pyrazoles, Diazepines, β‐Enaminones, and β‐Enamino Esters Using Silica‐Supported Sulfuric Acid as a Reusable Catalyst under Solvent‐Free Conditions.. ChemInform 40:33.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.