DOI: https://doi.org/10.9767/bcrec.13.1.963.82-88

Microwave Assisted Expeditious and Green Cu(II)-Clay Catalyzed Domino One-Pot Three Component Synthesis of 2H-indazoles

1Department of Chemistry, Govt., Degree College Boys, Sopore Jammu & Kashmir, 193201, India

2Department of Chemistry, University of Kashmir, Hazratbal, Srinagar, J&K, India

Received: 24 Feb 2017; Revised: 8 Aug 2017; Accepted: 23 Aug 2017; Available online: 22 Jan 2018; Published: 2 Apr 2018.
Editor(s): Y. H. Taufiq-Yap
Open Access Copyright (c) 2018 by Authors, Published by BCREC Group under http://creativecommons.org/licenses/by-sa/4.0.

Citation Format:
Cover Image
Abstract

A simple and efficient synthesis of 2H-indazoles is achieved from 2-primary amines, bromobenzaldehydes and sodium azide through domino condensation, C–N and N–N bond formations, catalyzed by a heterogeneous Cu(II)-Clay catalyst. The recyclable heterogeneous Cu(II)-Clay catalyst exhibited a remarkable activity for the title reaction without any additives. An assortment of structurally diverse 2H-indazoles were prepared in good to excellent yields from easily available starting materials by using this protocol. The Cu(II)-Clay catalyst was characterized by using X-Ray Diffraction (XRD), Scanning Electron Microscopy (SEM), and Brunauer-Emmett-Teller (BET) techniques.  

Fulltext View|Download
Keywords: 2H-indazoles; copper catalyst; multicomponent reaction; green synthesis; neat protocol

Article Metrics:

Article Info
Section: Original Research Articles
Language : EN
Recent articles
Catalytic Properties of Alumina-Supported Ruthenium, Platinum, and Cobalt Nanoparticles towards the Oxidation of Cyclohexane to Cyclohexanol and Cyclohexanone Zn-Mo/HZSM-5 Catalyst for Gasoil Range Hydrocarbon Production by Catalytic Hydrocracking of Ceiba pentandra oil Methyl Violet Degradation Using Photocatalytic and Photoelectrocatalytic Processes Over Graphite/PbTiO3 Composite A Computational Fluid Dynamics Study of Turbulence, Radiation, and Combustion Models for Natural Gas Combustion Burner Comparison of Five Advanced Oxidation Processes for Degradation of Pesticide in Aqueous Solution CeO2-TiO2 Photocatalyst: Ionic Liquid-Mediated Synthesis, Characterization, and Performance for Diisopropanolamine Visible Light Degradation Author Guideline (2017) Backmatter Frontmatter (Front Cover, Editorial Team, Indexing, and Table of Contents) More recent articles
  1. Kharitonov, V.G., Sharma, V.S., Magde, D., Koesling, D. (1999). Kinetics and Equilibria of Soluble Guanylate Cyclase Ligation by CO: Effect of YC-1. Biochemistry, 38: 10699-10706
  2. Morie, T., Harada, H., Kato, S. (1997). Convenient Synthesis of N-(2,2-dimethyl-1,3-dioxan-5-yl)-1 H-indazole-3-carboxamide, the Intermediate of 5-HT3 Receptor Antagonist. Synthetic Communication. 27: 559-566
  3. Fang, Y.L., Jin, C.L., Li, J.H., Tsang, M.H., Sheng, C.T., Che, M.T., Chin, C.W., Fong, C.C., Sheng, C.K. (2001). Synthesis of 1-benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents. Journal of Medicinal Chemistry, 44: 3746-3749
  4. Bonde, N., Gaikwad. (2004). Synthesis and Preliminary Evaluation of Some Pyrazine Containing Thiazolines and Thiazolidinones as Antimicrobial Agents. Bioorganic and Medicinal Chemistry, 12: 2151-2161
  5. Haung, L.J., Shih, M.L., Chen, H.S., Pan, S.L., Teng, C.M., Lee, F.Y., Kuo, S.C. (2006). Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as Novel Anti-angiogenic Agents. Bioorganic and Medicinal Chemistry, 14: 528-536
  6. Vijay, A.M., Antony, J.A., Chandrakumar, R.R., Koilraj, M., Sujatha, R., Shanmugsundram, P. (2008). Synthesis and Biological Activities of A Novel Series of Indazole Derivatives. Bioscience and Biotechnology Research, 5: 313-318
  7. Ye, M., Edmunds, A.J., Morris, J.A., Sale, D., Zhang, Y., Yu, J.Q. (2013). A Robust Protocol for Pd(II)-catalyzed C-3 Arylation of (1H) Indazoles and Pyrazoles: Total Synthesis of Nigellidine Hydrobromide. Chemical Science, 4: 2374-2379
  8. Yadav, J.S., Reddy, B.V.S., Sadasive, K., Satheesh, G. (2002). 1,4-Conjugate Addition of Allyltrimethylsilane to α,β-unsaturated Ketones. Tetrahedron Letters, 43: 9695-9697
  9. Kazzouli, S.E., Bouissane, L., Khouili, M., Guillaumet, G. (2005). Synthesis of 4-Substituted and 3,4-Disubstituted Indazole Derivatives by Palladium-Mediated Cross-Coupling Reactions. Tetrahedron Letters, 46: 6163-6167
  10. Nathan, E.G., Liuqing, W., Gary, E.A. (2014). Regioselective Synthesis of 2H-Indazoles Using a Mild, One-Pot Condensation–Cadogan Reductive Cyclization. Organic Letters, 16: 3114-3117
  11. Yuesi, F., Chunrui, W., Richard, C., Larock, Fenf.S. (2011). Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes. Journal of Organic Chemistry, 76: 8840-8851
  12. Goeminne, A., Scammells, P.J., Devine, S.M., Flynn, B.L. (2010). Richter cyclization and Co-cyclization Reactions of Triazene-masked Diazonium Ions. Tetrahedron Letters, 51: 6882-6885
  13. Kim, K.Y., Shin, J.T., Lee, K.S., Cho, C.G. (2004). Cu(I) Mediated One-pot Synthesis of Azobenzenes from Bis-Boc Aryl Hydrazines and Aryl Halides. Tetrahedron Letters, 45:117-120
  14. Kiyofumi, I., Mika, K., Takashi, Y., Yukari, A., Kou, H., Takao, S. (2007). Synthesis of 3-substituted Indazoles and Benzoisoxazoles via Pd-catalyzed Cyclization Reactions: Application to the Synthesis of Nigellicine. Tetrahedron, 63: 2695-2711
  15. Basuvaraj, S.K., Amarajothi, D., Kasi, P. (2014). K10 Montmorillonite Clays as Environmentally Benign Catalysts for Organic Reactions. Catalysis Science and Technology, 4: 2378-2396
  16. Dar, B.A., Varsha, S., Amrita, B., Wagay, M.A., Baldev, S. (2015). An Expeditious N,N-dibenzylation of Anilines under Ultrasonic Irradiation Conditions Using Low Loading Cu(II)-Clay Heterogeneous Catalyst. Tetrahedron Letters, 56: 136-141
  17. Dar, B.A., Nalini, P., Snehil, S., Purshotum, K., Farooqui, M., Baldev, S. (2015) Solvent-free, Scalable and Expeditious Synthesis of Benzanilides under Microwave Irradiation Using Clay Doped with Palladium Nanoparticles as A Recyclable and Efficient Catalyst. Green Chemistry Letters and Reviews, 8: 1-8
  18. Dar, B.A., Sara, K., Wani, T.A., Mir, M.A., Farooqui, M. (2015). Ceria-based Mixed Oxide Supported CuO: An Efficient Heterogeneous Catalyst for Conversion of Cellulose to Sorbitol. Green and Sustainable Chemistry, 5: 15-24
  19. Dar, B.A., Dangroo, N.A., Amit, G., Aarti, W., Khuroo, M.A., Vishwakarma, R.A., Baldev, S. (2014). Iodine Catalyzed Solvent-free Cross-dehydrogenative Coupling of Arylamines and H-Phosphonates for the Synthesis of N-Arylphosphoramidates under Atmospheric Conditions. Tetrahedron Letters, 55: 1544-1548
  20. Dar, B.A., Amrita, B., Amit, S., Parduman, R.S., Anish, L., Singh, A.P., Meena, S., Baldev, S. (2013). Ultrasound Promoted Efficient and Green Protocol for the Expeditious Synthesis of 1,4 Disubstituted 1,2,3-triazoles Using Cu(II) Doped Clay as Catalyst. Applied Clay Science, 80–81: 351-357
  21. Dar, B.A., Prince, B., Singh, A.P., Anish, L., Parduman, R.S., Meena, S., Baldev, S. (2013). Clay Entrapped Cu(OH)x as An Efficient Heterogeneous Catalyst for Ipso-Hydroxylation of Arylboronic Acids. Applied Catalysis A: General, 466: 60-67
  22. Mellouk, S., Cherifi, S., Sassi, M., Marouf-Khelifa, K., Bengueddach, A., Schott, J., Khelifa, A. (2009). Intercalation of Halloysite from Djebel Debagh (Algeria) and Adsorption of Copper Ions. Applied Clay Science, 44: 230-236
  23. Deng, C., Hu, H., Ge, X., Han, C., Zhao, D., Shao, G. (2011). One-pot Sonochemical Fabrication of Hierarchical Hollow CuO Submicrospheres. Ultrasonics Sonochemistry, 18: 932-937
  24. Zhao, D., Zhou, J., Liu, N. (2006). Preparation and Characterization of Mingguang Palygorskite Supported with Silver and Copper for Antibacterial Behaviour. Applied Clay Science, 33: 161-170
  25. Alvarez-Puebla, R.A., Aisa, C., Blasco, J.J., Echeverría, C., Mosquera, B., Garrido, J. (2004). Copper Heterogeneous Nucleation on A Palygorskitic Clay: an XRD, EXAFS and Molecular Modeling Study. Applied Clay Science, 25:103-110
  27. Yong, K., Manian, R.K., Namjin, P., Yumi, H., Sunwoo, L. (2011). Copper-Catalyzed, One-Pot, Three-Component Synthesis of Benzimidazoles by Condensation and C–N Bond Formation. Journal of Organic Chemistry, 76: 9577-9583

Last update:

No citation recorded.

Last update:

No citation recorded.