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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 20
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Original Articles

One-Pot, Three-Component Synthesis of 4H-Pyrans Using Cu(II) Oxymetasilicate

Majid M. Heravi Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, IranCorrespondence[email protected]
,
Yahya S. Beheshtiha Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
,
Zahra Pirnia Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
,
Samaheh Sadjadi Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
&
Mina Adibi Specialty Chemicals Research Department, Chemical and Petrochemical Division, Research Institute of Petroleum Industry, NIOC, Tehran, Iran
Pages 3663-3667 | Received 11 Jan 2009, Published online: 08 Sep 2009

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Abhijeet Mulik, Vishvanath Ghanwat, Pravin Hegade, Mukund Mali, D.-Y. Kim, Dae Sung Lee, Asif Shahzad, Surendra Shinde & Mohan Rajmane. (2023) A Novel Recyclable Bi-Mg-O Composite Nano-Catalyst Promoted Rapid and Efficient Synthesis of Spirooxindole and 4H-Pyran Derivatives. Polycyclic Aromatic Compounds 43:7, pages 6665-6678.
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Ali Maleki, Mojtaba Azizi & Zeynab Emdadi. (2018) A novel poly(ethyleneoxide)-based magnetic nanocomposite catalyst for highly efficient multicomponent synthesis of pyran derivatives. Green Chemistry Letters and Reviews 11:4, pages 573-582.
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Vaibhav W. Godse, Umesh R. Sonwane, Parmeshwar P. Pawar, Sahebrao S. Rindhe, Pravin S. Kendrekar & Rajendra P. Pawar. (2017) L-Pyrrolidine-2-Carboxylic Acid Sulfate: A New Ionic Liquid for the Synthesis of Bioactive Tetrahydrobenzo[b]pyrans. Organic Preparations and Procedures International 49:4, pages 363-369.
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Rufus Smits, Sergey Belyakov, Aiva Plotniece & Gunars Duburs. (2013) Synthesis of 4H-Pyran Derivatives Under Solvent-Free and Grinding Conditions. Synthetic Communications 43:4, pages 465-475.
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JitenderM. Khurana & Ankita Chaudhary. (2012) Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chemistry Letters and Reviews 5:4, pages 633-638.
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Articles from other publishers (39)

S. N. Shringare, K. R. Kadam, G. R. Pandhare, V. D. Murade, A. S. Waghmare, P. N. Kamble, N. R. Kamble & D. S. Wankhede. (2023) Heterogenization of Homogeneous Catalyst: An Improved Strategy for an Efficient Synthesis of Highly Substituted 4H-Pyran Scaffolds in Aqueous Based Media. Catalysis Letters 154:5, pages 1993-2007.
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Mjd Saleh Mariziq Al‐Sarhani, Wael Abdelgayed Ahmed Arafa, Amira Atef Ghoneim, Ibrahim O. Althobaiti, Modather Farok Hussein & Asmaa Kamal Mourad. (2024) Efficient One‐Pot Synthesis of 2‐Amino‐4 H pyran‐3‐carbonitriles Using Ionic Liquid: Reactions, Quantum‐Chemical Calculations, and Antiproliferative Activity . ChemistrySelect 9:1.
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Pooja Rana, Ranjana Dixit, Shivani Sharma, Sriparna Dutta, Sneha Yadav, Bhavya Arora, Bhawna Kaushik, Manoj B. Gawande & Rakesh K. Sharma. (2023) Preparation and characterization of the h -BN/Fe 3 O 4 /APTES-AMF/Cu II nanocomposite as a new and efficient catalyst for the one-pot three-component synthesis of 2-amino-4-aryl(or heteroaryl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4 H -chromene-3-carbonitriles . Nanoscale 15:7, pages 3482-3495.
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Nguyen Dinh Thanh, Do Son Hai, Le Thi Huyen, Vu Thi Tuyet Thuy, Do Tien Tung, Hoang Thi Kim Van, Vu Ngoc Toan, Nguyen Thi Kim Giang & Nguyen Minh Tri. (2022) Fe3O4-MNPs@MMT-K10: a reusable catalyst for synthesis of propargyl 4-aryl-4H-pyran-3-carboxyles via one‑pot three-component reaction under microwave-assisted solvent-free conditions. Research on Chemical Intermediates 49:2, pages 525-555.
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Lalhruaizela, Brilliant N. Marak, Biki Hazarika, Sunil Kumar Pandey, Ramesh Kataria & Ved Prakash Singh. (2022) Study of self-assembly features in 4H-pyrans: Synthesis, Hirshfeld surface, and energy framework analysis. Journal of Molecular Structure 1265, pages 133361.
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Negin Rostami, Mohammad G. Dekamin, Ehsan Valiey & Hamidreza Fanimoghadam. (2022) Chitosan-EDTA-Cellulose network as a green, recyclable and multifunctional biopolymeric organocatalyst for the one-pot synthesis of 2-amino-4H-pyran derivatives. Scientific Reports 12:1.
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Geetika Patel, Ashok Raj Patel, Gurupada Maity, Sajal Das, Shiv P. Patel & Subhash Banerjee. (2022) Fabrication of self-assembled Co3O4 nano-flake for one-pot synthesis of tetrahydrobenzo[b]pyran and 1,3-benzothazole derivatives. Current Research in Green and Sustainable Chemistry 5, pages 100258.
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Pardis H. Taghva & Hassan Kabirifard. (2021) Three-Component Efficient Synthesis of 2-Amino-3-cyano-4H-pyrans Catalyzed by Diammonium Hydrogen Phosphate in Aqueous Media. Current Organocatalysis 8:2, pages 187-194.
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Chandi C. Malakar, Virender Singh, Vipin Kumar, Dharmender Singh & Raghuram Gujjarappa. (2021) Efficient Approach towards the Polysubstituted 4H-Pyran Hybrid Quinolone Derivatives and Subsequent Copper-Catalyzed Hydroxylation of Haloarenes. HETEROCYCLES 102:3, pages 465.
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Pouya Ghamari Kargar, Ghodsieh Bagherzade & Hossein Eshghi. (2020) Novel biocompatible core/shell Fe 3 O 4 @NFC@Co( ii ) as a new catalyst in a multicomponent reaction: an efficient and sustainable methodology and novel reusable material for one-pot synthesis of 4 H -pyran and pyranopyrazole in aqueous media . RSC Advances 10:61, pages 37086-37097.
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Sainath Zangade & Pravinkumar Patil. (2020) A Review on Solvent-free Methods in Organic Synthesis. Current Organic Chemistry 23:21, pages 2295-2318.
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Mehri Salimi, Mohammad Ali Nasseri & Bahareh Niroomand Jazi. (2019) Cu(II)-immobilized on functionalized magnetic nano-fibrillated cellulose (Fe3O4@NFC/E-CHDA-CuII): a novel, efficient and magnetically nanocatalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives. Journal of the Iranian Chemical Society 16:10, pages 2221-2230.
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Ágnes Magyar & Zoltán Hell. (2018) One-pot, three-component, selective synthesis of the polyfunctionalized 4H-pyran and 4H-benzo[b]pyran derivatives in the presence of a highly efficient molecular sieve-supported zinc catalyst. Green Processing and Synthesis 7:4, pages 316-322.
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Fatemeh Ebrahimpour‐Malamir, Tayebeh Hosseinnejad, Razieh Mirsafaei & Majid M. Heravi. (2017) Synthesis, characterization and computational study of CuI nanoparticles immobilized on modified poly (styrene‐co‐maleic anhydride) as a green, efficient and recyclable heterogeneous catalyst in the synthesis of 1,4‐disubstituted 1,2,3‐triazoles via click reaction. Applied Organometallic Chemistry 32:1.
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Lu Chen, Jiaqi Lin, Bin Chen & Liqin Zhao. (2017) Sodium ethylene diamine tetraacetate catalyzed synthesis of chromene derivatives via multi-component reactions at low catalyst loading. Research on Chemical Intermediates 43:11, pages 6691-6700.
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Lu Chen, Sunan Bao, Lixiang Yang, Xian Zhang, Bin Li & Yibiao Li. (2017) Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol. Research on Chemical Intermediates 43:7, pages 3883-3891.
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B. Maleki, M. Baghayeri, S. Sheikh, S. Babaee & S. Farhadi. (2017) One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles. Russian Journal of General Chemistry 87:5, pages 1064-1072.
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Eliana Nope, José J. Martínez, Hugo A. Rojas, Ángel G. Sathicq & Gustavo P. Romanelli. (2016) Synthesis of mesoporous Ca-MCM catalysts and their use in suitable multicomponent synthesis of polyfunctionalized pyrans. Research on Chemical Intermediates 43:4, pages 2103-2118.
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Jalal Albadi & Azam Mansournezhad. (2016) Aqua-mediated multicomponent synthesis of various 4H-pyran derivatives catalyzed by poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst. Research on Chemical Intermediates 42:6, pages 5739-5752.
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Yogesh B. Wagh, Yogesh A. Tayade, Swapnil A. Padvi, Bhupesh S. Patil, Nilesh B. Patil & Dipak S. Dalal. (2015) A cesium fluoride promoted efficient and rapid multicomponent synthesis of functionalized 2-amino-3-cyano-4H-pyran and spirooxindole derivatives. Chinese Chemical Letters 26:10, pages 1273-1277.
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Malek Taher Maghsoodlou, Nourallah Hazeri, Mojtaba Lashkari, Fereshteh Nejad Shahrokhabadi, Behzad Naghshbandi, Mohammad Saeed Kazemi-doost, Mahnaz Rashidi, Fatemeh Mir, Mehrnoosh Kangani & Sajjad Salahi. (2014) Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives. Research on Chemical Intermediates 41:10, pages 6985-6997.
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R. Pagadala, S. Maddila & S. B. Jonnalagadda. (2014) An Efficient, Multicomponent, One‐pot Synthesis of Tetra Substituted Pyrans in Water. Journal of Heterocyclic Chemistry 52:4, pages 1226-1229.
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Pranjal P. Bora, Manisha Bihani & Ghanashyam Bez. (2015) Beyond enzymatic promiscuity: asymmetric induction by l -proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans . RSC Advances 5:62, pages 50597-50603.
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K. Aswin, S. Sheik Mansoor, K. Logaiya, S. P. N. Sudhan, V. Saleem Malik & H. Ramadoss. (2013) Reusable silica-bonded S-sulfonic acid catalyst for three-component synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes and 2-amino-4H-pyrans in aqueous ethanol. Research on Chemical Intermediates 40:8, pages 2583-2598.
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Sougata Santra, Matiur Rahman, Anupam Roy, Adinath Majee & Alakananda Hajra. (2014) Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[ b ]pyrans . Organic Chemistry International 2014, pages 1-8.
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Javad Safaei-Ghomi, Raheleh Teymuri, Hossein Shahbazi-Alavi & Abolfazl Ziarati. (2013) SnCl2/nano SiO2: A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans. Chinese Chemical Letters 24:10, pages 921-925.
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Meysam Amirnejad, Mohammad Reza Naimi-Jamal, Hesam Tourani & Hossein Ghafuri. (2013) A facile solvent-free one-pot three-component method for the synthesis of 2-amino-4H-pyrans and tetrahydro-4H-chromenes at ambient temperature. Monatshefte für Chemie - Chemical Monthly 144:8, pages 1219-1225.
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Manisha Bihani, Pranjal P. Bora & Ghanashyam Bez. (2013) Synthesis of Polyfunctionalized 4 H -Pyrans . Journal of Chemistry 2013, pages 1-7.
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Subhash Banerjee & Arijit Saha. (2013) Free-ZnO nanoparticles: a mild, efficient and reusable catalyst for the one-pot multicomponent synthesis of tetrahydrobenzo[b]pyran and dihydropyrimidone derivatives. New Journal of Chemistry 37:12, pages 4170.
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Mohamed H. Elnagdi, Kamal U. Sadek & Moustafa S. Moustafa. 2013. 241 312 .
Samad Khaksar, Ahmad Rouhollahpour & Saeed Mohammadzadeh Talesh. (2012) A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium. Journal of Fluorine Chemistry 141, pages 11-15.
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Mahesh Shivaji Pandharpatte, Khudbudin Baban Mulani & Nazeruddin Nasiruddin Gulam Mohammed. (2012) Microwave Promoted, Sodium Acetate Catalyzed One Pot Synthesis of Poly Functionalized 4H‐Pyrans. Journal of the Chinese Chemical Society 59:5, pages 645-649.
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Umesh R. Pratap, Dhanaji V. Jawale, Prashant D. Netankar & Ramrao A. Mane. (2011) Baker’s yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans. Tetrahedron Letters 52:44, pages 5817-5819.
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Dong Fang, Jin-ming Yang, Hua-bin Zhang & Chang-mei Jiao. (2011) Synthesis of 4H-pyrans catalyzed by thermol-regulated PEG1000-based ionic liquid/EM. Journal of Industrial and Engineering Chemistry 17:3, pages 386-388.
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Majid M. Heravi, Yahya S. Beheshtiha, Zahra Pirnia, Samaheh Sadjadi & Mina Adibi. (2010) ChemInform Abstract: One‐Pot, Three‐Component Synthesis of 4H‐Pyrans Using Cu(II) Oxymetasilicate.. ChemInform 41:14.
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