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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 15
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Original Articles

Hypervalent Iodine Oxidation of 1, 3, 5-Trisubstituted Pyrazolines: A Facile Synthesis of 1,3,5-Trisubstituted Pyrazoles

Shiv P. Singh Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, Haryana, INDIA
,
Dalip Kumar Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, Haryana, INDIA
,
Om Prakash Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, Haryana, INDIA
&
R. P. Kapoor Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, Haryana, INDIA
Pages 2683-2689 | Received 21 Jan 1997, Published online: 22 Aug 2006

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Ranjana Aggarwal, Gulshan Singh & Suresh Kumar. (2021) Molecular iodine mediated transition-metal-free oxidative dehydrogenation of 4,7-dihydropyrazolo[3,4-b]pyridines. Synthetic Communications 51:23, pages 3601-3609.
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Behrooz Maleki, Fatemeh Barakchi Tabrizy, Reza Tayebee & Mehdi Baghayeri. (2019) Oxidative Aromatization of 1,3,5-trisubstituted 2-pyrazolines Using Oxalic Acid/Sodium Nitrite System. Polycyclic Aromatic Compounds 39:2, pages 93-98.
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SumitV. Gamapwar, NileshP. Tale & NandkishorN. Karade. (2012) Dess–Martin Periodinane–Mediated Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines. Synthetic Communications 42:17, pages 2617-2623.
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VidyaG. Desai, PoojaC. Satardekar, Sampada Polo & Kashinath Dhumaskar. (2012) Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles. Synthetic Communications 42:6, pages 836-842.
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Yunkui Liu, Dajie Mao, Shaojie Lou, Jianqing Qian & Zhen-Yuan Xu. (2009) Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines Using Hydrogen Tetrachloroaurate as Catalyst Under an Oxygen Atmosphere. Organic Preparations and Procedures International 41:3, pages 237-242.
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Shashikanth Ponnala & Devi Prasad Sahu. (2006) Iodine‐Mediated Synthesis of 2‐Arylbenzoxazoles, 2‐Arylbenzimidazoles, and 1,3,5‐Trisubstituted Pyrazoles. Synthetic Communications 36:15, pages 2189-2194.
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Davood Azarifar & Behrooz Maleki. (2005) Microwave‐Assisted Aromatization of 1,3,5‐Trisubstituted 2‐Pyrazolines by Bi(NO3)3 · 5H2O, as a Novel and Convenient Oxidizing Agent. Synthetic Communications 35:19, pages 2581-2585.
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Ramin Ghorbani-Vaghei, Davood Azarifar, Ardeshir Khazaei & Behrooz Maleki. (2004) N,N′,N,N′-TETRABROMO-BENZENE-1,3-DISULFONYLAMIDE AS A NOVEL REAGENT FOR OXIDATIVE AROMATIZATION OF 1,3,5-TRISUBSTITUTED PYRAZOLINES UNDER HETEROGENEOUS AND SOLVENT-FREE CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:9, pages 1877-1881.
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Stefan J. Pastine, Wayne Kelley$suffix/text()$suffix/text(), Jennifer J. Bear, J. Nathan Templeton$suffix/text()$suffix/text() & Charles F. Beam. (2001) THE PREPARATION OF 3-(2-PHENYLETHENYL)-1H-PYRAZOLES FROM DILITHIATED (3E)-4-PHENYL-3-BUTEN-2-ONE HYDRAZONES. Synthetic Communications 31:4, pages 539-548.
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Limei Gao, Ruijie Shi, Yuting Tian, Xi Luo, Yongsheng Zheng & Qiang Wang. (2021) Synthesis of Pyrazoles through [3+2] Cyclization of Nitrile Imines with Cinnamaldehydes Followed by Air Oxidation. ChemistrySelect 6:45, pages 12838-12842.
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Rimpy Bhatia, Kulbir Kadyan, Meenakshi Duhan, Meena Devi, Rahul Singh, Ramesh C. Kamboj & Parvin Kumar. (2019) A Serendipitous Synthesis: SiO 2 ‐HNO 3 Mediated Oxidative Aromatization and Regioselective Nitration of 1,3,5‐Trisubstituted‐4,5‐Dihydro‐1 H ‐Pyrazoles . ChemistrySelect 4:35, pages 10417-10424.
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Sesuraj Babiola Annes, Rajamani Rajmohan, Subburethinam Ramesh & Pothiappan Vairaprakash. (2019) Visible light mediated metal-free oxidative aromatization of 1,3,5-trisubstituted pyrazolines. Tetrahedron Letters 60:34, pages 150932.
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Pan Ye, Deng-Hui Wang, Bin Chen, Qing-Yuan Meng, Chen-Ho Tung & Li-Zhu Wu. (2016) Visible light catalyzed aromatization of 1,3,5-triaryl-2-pyrazolines by platinum(II) polypyridyl complex under oxidant-free condition. Science China Chemistry 59:2, pages 175-179.
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Kaveh Khosravi. (2014) Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN. Research on Chemical Intermediates 41:8, pages 5253-5260.
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Dipanwita Banerjee, Utpal Kayal, Rajiv Karmakar & Gourhari Maiti. (2014) 3,4-Dihydro-2H-pyran promoted aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines. Tetrahedron Letters 55:38, pages 5333-5337.
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Jin Yu, Ko Hoon Kim, Hye Ran Moon & Jae Nyoung Kim. (2014) Facile One-Pot Synthesis of 1,3,5-Trisubstituted Pyrazoles from α,β-Enones. Bulletin of the Korean Chemical Society 35:6, pages 1692-1696.
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Guddekoppa S. Ananthnag, Adithya Adhikari & Maravanji S. Balakrishna. (2014) Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines. Catalysis Communications 43, pages 240-243.
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Vivek T. Humne, Kamal Hasanzadeh & Pradeep D. Lokhande. (2012) Selective O-deallylation of dihydropyrazoles by molecular iodine in the presence of active N-allyl and formyl groups. Research on Chemical Intermediates 39:2, pages 585-595.
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Sneha Naik & Vidya Desai. (2013) Use of Solid-Supported Reagents towards Synthesis of 2-Arylbenzoxazole, 3, 5-Diarylisoxazole and 1, 3, 5-Triarylpyrazole. Green and Sustainable Chemistry 03:01, pages 1-7.
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V. Kameshwara Rao, Rakesh Tiwari, Bhupender S. Chhikara, Amir Nasrolahi Shirazi, Keykavous Parang & Anil Kumar. (2013) Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities. RSC Advances 3:35, pages 15396.
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Naoufel Ben Hamadi & Moncef Msaddek. (2011) The Swern Oxidation: First example of direct oxidation of 2-pyrazolines with “activated” DMSO. Comptes Rendus. Chimie 14:11, pages 997-1001.
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Dhanaji V. Jawale, Umesh R. Pratap, Jyotirling R. Mali & Ramrao A. Mane. (2011) Silica chloride catalyzed one-pot synthesis of fully substituted pyrazoles. Chinese Chemical Letters.
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Nandkishor N. Karade, Sumit V. Gampawar, Nilesh P. Tale & Sanjay B. Kedar. (2010) Mild and efficient oxidative aromatization of 4‐substituted‐1,4‐dihydropyrimidines using (diacetoxyiodo)benzene. Journal of Heterocyclic Chemistry 47:3, pages 740-744.
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Davood Azarifar & Kaveh Khosravi. (2013) Oxidative Aromatization of 1,3,5‐Trisubstituted 4,5‐Dihydro‐1H‐Pyrazoles Efficiently by Tetrabromine‐1,3,5,7‐Tetrazatricyclo[3.3.1.1 3,7 ]Decane Complex, Br 4 ‐Tatcd, as a Novel Reagent both Under Microwave Irradiation and at Room Temperature . Journal of the Chinese Chemical Society 56:1, pages 43-46.
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Nandkishor N. Karade, Sumit V. Gampawar, Jeevan M. Kondre & Girdharilal B. Tiwari. (2008) A novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide for the facile oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Letters 49:47, pages 6698-6700.
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Gang Su, Wen Tao Wu, Jian Tao Wang & Long Min Wu. (2008) TBPA+ mediated aromatization of 1,3,5-trisubstituted pyrazolines. Chinese Chemical Letters 19:9, pages 1013-1016.
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H. Adibi, A. R. Hajipour & H. Jafari. (2008) Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions. Chemistry of Heterocyclic Compounds 44:7, pages 802-806.
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Young Tak Lee & Young Keun Chung. (2008) Silver(I)-Catalyzed Facile Synthesis of Pyrazoles From Propargyl N -Sulfonylhydrazones . The Journal of Organic Chemistry 73:12, pages 4698-4701.
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Lingzhi Chai, Yankai Zhao, Qiuju Sheng & Zhong-Quan Liu. (2006) Aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines with HIO3 and I2O5 in water. Tetrahedron Letters 47:52, pages 9283-9285.
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Bing Han, Zhengang Liu, Qiang Liu, Li Yang, Zhong-Li Liu & Wei Yu. (2006) An efficient aerobic oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines. Tetrahedron 62:11, pages 2492-2496.
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