European Journal of Chemistry 2011, 2(2), 223-228. doi:10.5155/eurjchem.2.2.223-228.336

A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives


Pradeep Lokhande (1) , Kamal Hasanzadeh (2,*) , Shankaraiah Guruvaiah Konda (3)

(1) Department of Chemistry, Organic Research Chemistry, University of Pune, Pune-411007, India
(2) Department of Chemistry, Organic Research Chemistry, University of Pune, Pune-411007, India
(3) Department of Chemistry, Organic Research Chemistry, University of Pune, Pune-411007, India
(*) Corresponding Author

Received: 21 Nov 2010, Accepted: 17 Feb 2011, Published: 30 Jun 2011

Abstract


A convenient protocol for the efficient synthesis of 2-arylpyrazolo[4,3-c]coumarins is described. The synthesis route involves molecular iodine catalyzed oxidative cyclization of 1-phenyl-3-(2'-hydroxyaryl)-4-formyl pyrazoles in dimethylsulfoxide. During the lactonisation of 4-formylpyrazoles, we found that iodine was incorporated into the unsubstituted O/P position of the 3-(2'-hydroxyaryl) group. Under similar conditions o-allyloxy derivative of pyrazoles gave same corresponding lactone derivatives by deallylation, lactonisation, and iodination in one step.

2_2_223_228_800


Keywords


Iodine; Lactonisation; Deallylation; 2-Arylpyrazolo[4,3-c]coumarins; Oxidation; Iodination

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DOI: 10.5155/eurjchem.2.2.223-228.336

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[1]. Khalid Karrouchi, Smaail Radi, Youssef Ramli, Jamal Taoufik, Yahia Mabkhot, Faiz Al-aizari, M’hammed Ansar
Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review
Molecules  23(1), 134, 2018
DOI: 10.3390/molecules23010134
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[2]. Assia Sid, Nouara Ziani, Ouafa Demmen-Debbih, Mahieddine Mokhtari, Kaddour Lamara
Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one
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[3]. Vivek T. Humne, Kamal Hasanzadeh, Pradeep D. Lokhande
Selective O-deallylation of dihydropyrazoles by molecular iodine in the presence of active N-allyl and formyl groups
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DOI: 10.1007/s11164-012-0581-2
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[4]. Avinash M. Patil, Dayanand A. Kamble, Pradeep D. Lokhande
A Metal-Free Iodination of Aryl Ethers and Phenols Using I2
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[5]. Anshu Jain, Ragini Gupta, Madhu Agarwal
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DOI: 10.1002/jhet.2884
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[6]. Sultan Nacak Baytas, Nazan Inceler, Akın Yılmaz
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DOI: 10.1007/s00044-013-0505-8
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[7]. Tarik E. Ali, Magdy A. Ibrahim, Zeinab M. El-Gendy, Eman M. El-Amin
4,6-Diacetylresorcinol in Heterocyclic Synthesis, Part I: Synthesis and Biological Evaluation of Some New Linearly and Angularly Substituted Pyrano[3,2-g] Chromenes via Vilsmeier–Haack Formylation of 4,6-Diacetylresorcinol, Its Schiff Bases, and Hydrazones
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How to cite


Lokhande, P.; Hasanzadeh, K.; Konda, S. Eur. J. Chem. 2011, 2(2), 223-228. doi:10.5155/eurjchem.2.2.223-228.336
Lokhande, P.; Hasanzadeh, K.; Konda, S. A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives. Eur. J. Chem. 2011, 2(2), 223-228. doi:10.5155/eurjchem.2.2.223-228.336
Lokhande, P., Hasanzadeh, K., & Konda, S. (2011). A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives. European Journal of Chemistry, 2(2), 223-228. doi:10.5155/eurjchem.2.2.223-228.336
Lokhande, Pradeep, Kamal Hasanzadeh, & Shankaraiah Guruvaiah Konda. "A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives." European Journal of Chemistry [Online], 2.2 (2011): 223-228. Web. 22 Sep. 2019
Lokhande, Pradeep, Hasanzadeh, Kamal, AND Konda, Shankaraiah. "A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.2.223-228.336

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