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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 9
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Original Articles

Synthesis of Novel 1-H-Pyrazole-4-carboxylic Acid Esters by Conventional and Microwave Assisted Vilsmeier Cyclization of Hydrazones

Radhakrishnan Sridhar Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai, India
&
Paramasivan T. Perumal Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai, IndiaCorrespondence[email protected]
Pages 1483-1488 | Received 15 Jun 2002, Published online: 16 Aug 2006

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Sumit Sood, Meena Kumari, Poonam Kumari, Anil Kumar & Karan Singh. (2020) Convenient OPC-VH Mediated Synthesis of 4-Functional Pyrazoles. Organic Preparations and Procedures International 52:6, pages 530-536.
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Tuncay Tunç, Habibe Tezcan, Ertan Şahin & Nefise Dilek. (2012) Synthesis, Crystal Structure, and Spectroscopic Studies of N-(4-Bromobenzylidene)-N′-(2-Pyridyl) Hydrazine Schiff Base Molecule. Molecular Crystals and Liquid Crystals 552:1, pages 194-208.
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Weike Su, Yiyi Weng, Ling Jiang, Yanyan Yang, Linyao Zhao, Zhiwei Chen, Zhenhua Li & Jianjun Li. (2010) Recent Progress in the Use of Vilsmeier-Type Reagents. Organic Preparations and Procedures International 42:6, pages 503-555.
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Amélia P. Rauter, José A. Figueiredo, Maria I. Ismael & Jorge Justino. (2004) Synthesis of New Pseudo‐C‐Nucleosides Containing Pyrazole Rings in their Structure. Journal of Carbohydrate Chemistry 23:8-9, pages 513-528.
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Monika Kamboj, Sangeeta Bajpai, Monika Yadav & Surabhi Singh. (2023) Microwave Radiations: A Green Approach to the Synthesis of Five- Membered Heterocyclic Compounds. Current Green Chemistry 10:1, pages 57-72.
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Anupama Chauhan, Ajay Kumar & Anju Goel. (2022) A Retrospective Study of Synthesis, Structure-Activity Relationship and Antimicrobial Activity of 4-Formyl Pyrazole Containing Isoniazid Moiety. Asian Journal of Organic & Medicinal Chemistry 7:1, pages 11-22.
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Ismail A. Abdelhamid, Mohamed R. Shaaban & Ahmed H.M. Elwahy. 2022. 171 223 .
Alireza Kohzadian, Hossein Filian, Zahra Kordrostami, Abdolkarim Zare & Arash Ghorbani-Choghamarani. (2020) A simple, rapid and effective protocol for synthesis of bis(pyrazolyl)methanes using nickel–guanidine complex immobilized on MCM-41. Research on Chemical Intermediates 46:3, pages 1941-1953.
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Renu Bala, Vandana Devi, Pratibha Singh, Navjot Kaur, Pawandeep Kaur, Anil Kumar, Ajar Nath Yadav & Karan Singh. (2019) Regioselective Synthesis of Potent 4,5,6,7-Tetrahydroindazole Derivatives via Microwave-assisted Vilsmeier-Haack Reaction and their Antioxidant Activity Evaluation. Letters in Organic Chemistry 16:3, pages 194-201.
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Aneet Kamal Kaur, Renu Bala, Poonam Kumari, Sumit Sood & Karan Singh. (2019) Microwave Assisted Vilsmeier-Haack Reaction on Substituted Cyclohexanone Hydrazones: Synthesis of Novel 4,5,6,7-Tetrahydroindazole Derivatives. Letters in Organic Chemistry 16:3, pages 170-175.
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Rosa M. Claramunt, Dolores Santa María, Ibon Alkorta & José Elguero. (2018) The Structure of N -phenyl-pyrazoles and Indazoles: Mononitro, Dinitro, and Trinitro Derivatives . Journal of Heterocyclic Chemistry 55:1, pages 44-64.
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Shuddhodan Narhari Kadam, Ajay Niwruttirao Ambhore, Milind Vithalrao Gaikwad, Rahul Datta Kamble, Shrikant Vasantappa Hese, Madhav Janardan Hebade & Bhaskar Sadashiv Dawane. (2016) Microwave assisted multicomponent reaction: An environmentally benign protocol for the synthesis of substituted imidazo[2,1-b]thiazole-2-carbohydrazide derivatives under solvent free condition. European Journal of Chemistry 7:4, pages 431-435.
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Sergey P. Ivonin, Bohdan B. Kurpil’, Oleksandr O. Grygorenko & Dmitry M. Volochnyuk. (2014) Reaction of hydrazones derived from active methylene compounds with Vilsmeier–Haack reagent. Monatshefte für Chemie - Chemical Monthly 145:12, pages 2011-2017.
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Sergey P. Ivonin, Bohdan B. Kurpil’, Eduard B. Rusanov, Oleksandr O. Grygorenko & Dmitry M. Volochnyuk. (2014) N-Alkylhydrazones of aliphatic ketones in the synthesis of 1,3,4-trisubstituted non-symmetric pyrazoles. Tetrahedron Letters 55:14, pages 2187-2189.
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Yogesh Daulat Dhage, Hiroki Daimon, Cheng Peng, Taichi Kusakabe, Keisuke Takahashi, Yuichiro Kanno, Yoshio Inouye & Keisuke Kato. (2014) Pd( ii )-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates . Org. Biomol. Chem. 12:43, pages 8619-8626.
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Chun-Hsi Chang, Henry J. Tsai, Yu-Ying Huang, Hui-Yi Lin, Li-Ya Wang, Tian-Shung Wu & Fung Fuh Wong. (2013) Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents. Tetrahedron 69:4, pages 1378-1386.
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Hussain Ali Soleiman, Ali Kamel Khalafallah & Hana'a Abd-Ellatif. (2012) Synthesis and studies of pyrazolo[3,4-b]pyridin-4-one derivatives. European Journal of Chemistry 3:3, pages 316-321.
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Xiaohui Yang, Pinghu Zhang, Yonghong Zhou, Junsong Wang & Hongjun Liu. (2012) Synthesis and Antioxidant Activities of Novel 4,4′‐Arylmethylene‐bis(1 H ‐pyrazole‐5‐ol)s from Lignin . Chinese Journal of Chemistry 30:3, pages 670-674.
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Hoong-Kun Fun, Ching Kheng Quah, Nithinchandra & Balakrishna Kalluraya. (2011) 4-[2-(4-Chlorophenyl)hydrazinylidene]-3-methyl-1 H -pyrazol-5(4 H )-one . Acta Crystallographica Section E Structure Reports Online 67:10, pages o2670-o2670.
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Fung Fuh Wong & Yu-Ying Huang. (2011) Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide. Tetrahedron 67:21, pages 3863-3867.
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Hoong-Kun Fun, Safra Izuani Jama Asik, Ibrahim Abdul Razak, Shobhitha Shetty & Balakrishna Kalluraya. (2011) 3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-4,5-dihydro-1 H -pyrazole-1-carbothioamide . Acta Crystallographica Section E Structure Reports Online 67:4, pages o928-o928.
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Hoong-Kun Fun, Wan-Sin Loh & Suresh P. Nayak. (2010) 4-Methoxybenzaldehyde (5-bromopyrimidin-2-yl)hydrazone monohydrate. Acta Crystallographica Section E Structure Reports Online 66:9, pages o2467-o2467.
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Jia Hao Goh, Hoong-Kun Fun, Nithinchandra, B. Kalluraya & N. Satheesh Rai. (2010) [3-(5-Nitro-2-furyl)-1-phenyl-1 H -pyrazol-4-yl](phenyl)methanone . Acta Crystallographica Section E Structure Reports Online 66:5, pages o1229-o1230.
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Hoong-Kun Fun, Chin Sing Yeap, K. V. Sujith & B. Kalluraya. (2009) N ′-[( E )-4-Chlorobenzylidene]-2-(4-isobutylphenyl)propanohydrazide . Acta Crystallographica Section E Structure Reports Online 65:6, pages o1196-o1197.
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Hoong-Kun Fun, Ching Kheng Quah, K. V. Sujith & B. Kalluraya. (2009) N ′-[( E )-4-Bromobenzylidene]-2-(4-isobutylphenyl)propanohydrazide . Acta Crystallographica Section E Structure Reports Online 65:6, pages o1184-o1185.
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Ke-Lai Li, Zong-Bo Du, Can-Cheng Guo & Qing-Yun Chen. (2009) Regioselective Syntheses of 2- and 4-Formylpyrido[2,1- b ]benzoxazoles . The Journal of Organic Chemistry 74:9, pages 3286-3292.
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Hoong-Kun Fun, Suchada Chantrapromma, K. V. Sujith & B. Kalluraya. (2009) 2-(4-Isobutylphenyl)- N ′-[1-(4-nitrophenyl)ethylidene]propanohydrazide . Acta Crystallographica Section E Structure Reports Online 65:3, pages o445-o445.
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Hoong-Kun Fun, Samuel Robinson Jebas, K. V Sujith & B. Kalluraya. (2008) N ′-[( E )-1-(4-Chlorophenyl)ethylidene]-2-[4-(2-methylpropyl)phenyl]propanohydrazide . Acta Crystallographica Section E Structure Reports Online 65:1, pages o17-o18.
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Hoong-Kun Fun, Samuel Robinson Jebas, K. V. Sujith & B. Kalluraya. (2008) N ′-[( Z )-4-Methylbenzylidene]-4-nitrobenzohydrazide monohydrate . Acta Crystallographica Section E Structure Reports Online 64:12, pages o2338-o2338.
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Hoong-Kun Fun, K. V. Sujith, P. S. Patil, B. Kalluraya & Suchada Chantrapromma. (2008) N ′-[( E )-1-Phenylethylidene]benzohydrazide . Acta Crystallographica Section E Structure Reports Online 64:10, pages o1961-o1962.
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V.V.V.N.S. Rama Rao, B.P.V. Lingaiah, R. Yadla, P. Shanthan Rao, K. Ravikumar, G.Y.S.K. Swamy & K. Narsimulu. (2009) Synthesis of fluorine containing N ‐benzyl‐1,2,3‐triazoles and N ‐methyl‐pyrazoles from conjugated alkynes . Journal of Heterocyclic Chemistry 43:3, pages 673-679.
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Mirjana Eckert-Maksic, Irena Zrinski & Marina Juribasic. (2006) Microwave-Assisted Synthesis of Pyrazoles by 1,3-Dipolar Cycloaddition of Diazo Compounds to Acetylene Derivatives. HETEROCYCLES 68:9, pages 1961.
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Radhakrishnan Sridhar & Paramasivan T. Perumal. (2005) A new protocol to synthesize 1,4-dihydropyridines by using 3,4,5-trifluorobenzeneboronic acid as a catalyst in ionic liquid: synthesis of novel 4-(3-carboxyl-1H-pyrazol-4-yl)-1,4-dihydropyridines. Tetrahedron 61:9, pages 2465-2470.
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R. Sridhar, G. Sivaprasad & P. T. Perumal. (2009) An efficient synthesis of 1‐ H ‐pyrazole‐4‐carboxylic acid esters with vilsmeier reagent under neat conditions . Journal of Heterocyclic Chemistry 41:3, pages 405-408.
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Radhakrishnan Sridhar & Paramasivan T. Perumal. (2003) Synthesis of Novel 1-H-Pyrazole-4-carboxylic Acid Esters by Conventional and Microwave Assisted Vilsmeier Cyclization of Hydrazones.. ChemInform 34:34.
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