ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
-
Selvaraj Roopan
und
Fazlur Khan
Abstract
An efficient ligand-free cross-coupling reaction of 2-chloro-3-(chloromethyl)benzo[h]quinoline with N-heterocycles such as piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate using a catalytic amount of ZnO nanorods as a recyclable catalyst and KOH as the base in DMSO under reflux at 110°C is reported.
[1] Alonso, F., Riente, P., & Yus, M. (2008). Hydrogen-transfer reduction of carbonyl compounds promoted by nickel nanoparticles. Tetrahedron, 64, 1847–1852. DOI: 10.1016/j.tet.2007.11.093. http://dx.doi.org/10.1016/j.tet.2007.11.09310.1016/j.tet.2007.11.093Suche in Google Scholar
[2] Chinchilla, R., & Nájera, C. (2007). The Sonogashira reaction: A booming methodology in synthetic organic chemistry. Chemical Reviews, 107, 874–922. DOI: 10.1021/cr050992x. http://dx.doi.org/10.1021/cr050992x10.1021/cr050992xSuche in Google Scholar PubMed
[3] Eltsov, O. S., Mokrushin, V. S., Rybalova, T. V., Gatilov, Y. V., & Tkachev, A. V. (2000). N-alkylation in the reactions of 5-imidazolylphenylthiourea with alkylhalides and chloroacetone. Mendeleev Communications, 10, 233–234. DOI: 10.1070/MC2000v010n06ABEH001324. http://dx.doi.org/10.1070/MC2000v010n06ABEH00132410.1070/MC2000v010n06ABEH001324Suche in Google Scholar
[4] Kawano, T., & Imai, H. (2008). A simple preparation technique for shape-controlled zinc oxide nanoparticles: Formation of narrow size-distributed nanorods using seeds in aqueous solutions. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 319, 130–135. DOI: 10.1016/j.colsurfa.2007.05.019. http://dx.doi.org/10.1016/j.colsurfa.2007.05.01910.1016/j.colsurfa.2007.05.019Suche in Google Scholar
[5] Khan, F. N., Subashini, R., Kumar, R., Hathwar, V. R., & Ng, S. W. (2009a). 2-Chloroquinoline-3-carbaldehyde. Acta Crystallographica Section E, E65, o2710. DOI: 10.1107/S160053680 9040665. http://dx.doi.org/10.1107/S160053680904066510.1107/S1600536809040665Suche in Google Scholar PubMed PubMed Central
[6] Khan, F. N., Subashini, R., Roopan, S. M., Hathwar, V. R., & Ng, S. W. (2009b). 2-Chloro-6-methylquinoline-3-carbaldehyde. Acta Crystallographica Section E, E65, o2686. DOI: 10.1107/S1600536809040653. http://dx.doi.org/10.1107/S160053680904065310.1107/S1600536809040653Suche in Google Scholar PubMed PubMed Central
[7] Manivel, P., Roopan, S. M., & Khan, F. N. (2008). Synthesis of O-substituted benzophenones by Grignard reaction of 3-substituted isocoumarins. Journal of the Chilean Chemical Society, 53, 1609–1610. DOI: 10.4067/S0717-97072008000300012. http://dx.doi.org/10.4067/S0717-9707200800030001210.4067/S0717-97072008000300012Suche in Google Scholar
[8] Manivel, P., Roopan, S. M., Kumar, D. P., & Khan, F. N. (2009). Isocoumarin thioanalogues as potential antibacterial agents. Phosphorus, Sulfur, and Silicon and the Related Elements, 184, 2576–2582. DOI: 10.1080/10426500802529507. http://dx.doi.org/10.1080/1042650080252950710.1080/10426500802529507Suche in Google Scholar
[9] Mirjafary, Z., Saeidian, H., Sadeghi, A., & Moghaddam, F. M. (2008). ZnO nanoparticles: An efficient nanocatalyst for the synthesis of β-acetamido ketones/esters via a multicomponent reaction. Catalysis Communications, 9, 299–306. DOI: 10.1016/j.catcom.2007.06.018. http://dx.doi.org/10.1016/j.catcom.2007.06.01810.1016/j.catcom.2007.06.018Suche in Google Scholar
[10] Nacro, K., Zha, C., Guzzo, P. R., Herr, R. J., Peace, D., & Friedrich, T. D. (2007). Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives. Bioorganic & Medicinal Chemistry, 15, 4237–4246. DOI: 10.1016/j.bmc.2007.03.067. http://dx.doi.org/10.1016/j.bmc.2007.03.06710.1016/j.bmc.2007.03.067Suche in Google Scholar PubMed
[11] Richards, R., Li, W., Decker, S., Davidson, C., Koper, O., Zaikovski, V., Volodin, A., Rieker, T., & Klabunde, K. J. (2000). Consolidation of metal oxide nanocrystals. Reactive pellets with controllable pore structure that represent a new family of porous, inorganic materials. Journal of the American Chemical Society, 122, 4921–4925. DOI: 10.1021/ja994383g. http://dx.doi.org/10.1021/ja994383g10.1021/ja994383gSuche in Google Scholar
[12] Roopan, S. M., & Khan, F. R. N. (2009). Synthesis, antioxidant, hemolytic and cytotoxicity activity of AB ring core of mappicine. ARKIVOC, xiii, 161–169. 10.3998/ark.5550190.0010.d14Suche in Google Scholar
[13] Roopan, S. M., Khan, F. R. N., & Mandal, B. K. (2010). Fe nano particles mediated C-N bond forming reaction: Regioselective synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3H)ones. Tetrahedron Letters, 51, 2309–2311. DOI: 10. 1016/j.tetlet.2010.02.128. http://dx.doi.org/10.1016/j.tetlet.2010.02.12810.1016/j.tetlet.2010.02.128Suche in Google Scholar
[14] Roopan, S. M., Khan, F. N., Subashini, R., Hathwar, V. R., & Ng, S. W. (2009a). 2-Chlorobenzo[h]quinoline-3-carbaldehyde. Acta Crystallographica Section E, E65, o2711. DOI: 10.1107/S1600536809040720. http://dx.doi.org/10.1107/S160053680904072010.1107/S1600536809040720Suche in Google Scholar PubMed PubMed Central
[15] Roopan, S. M., Khan, F. N., Vijetha, M., Hathwar, V. R., & Ng, S. W. (2009b). Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate. Acta Crystallographica Section E, E65, o2982. DOI: 10.1107/S1600536809045334. http://dx.doi.org/10.1107/S160053680904533410.1107/S1600536809045334Suche in Google Scholar PubMed PubMed Central
[16] Roopan, S. M., Maiyalagan, T., & Khan, F. N. (2008). Solvent-free syntheses of some quinazolin-4(3H)-ones derivatives. Canadian Journal of Chemistry, 86, 1019–1025. DOI: 10.1139/V08-149. http://dx.doi.org/10.1139/V08-14910.1139/v08-149Suche in Google Scholar
[17] Sivasubramanian, G., & Parameswaran, V. R. (2007). Oxidation of N-heterocyclics: A green approach. Journal of Heterocyclic Chemistry, 44, 1223–1230. DOI: 10.1002/jhet.5570440601. http://dx.doi.org/10.1002/jhet.557044060110.1002/jhet.5570440601Suche in Google Scholar PubMed PubMed Central
© 2010 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- A deuterium-palladium electrode as a new sensor in non-aqueous solutions: potentiometric titration of weak acids in acetonitrile and benzonitrile
- Chemical variability of Artemisia herba-alba Asso essential oils from East Morocco
- Ag and Cu loaded on TiO2/graphite as a catalyst for Escherichia coli-contaminated water disinfection
- Direct electrochemistry and electrocatalysis of horseradish peroxidase immobilized in hyaluronic acid and single walled carbon nanotubes composite film
- Biological buffered saline solution as solvent in agar-carbomer hydrogel synthesis
- GC/MS analysis of gaseous degradation products formed during extrusion blow molding process of PE films
- Preparation, spectral, thermal, and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylate complexes with methyl 3-pyridylcarbamate and phenazone
- Polyamidoamine dendrimer and dextran conjugates: preparation, characterization, and in vitro and in vivo evaluation
- Morphological characteristics of modified freeze-dried poly(N-isopropylacrylamide) microspheres studied by optical microscopy, SEM, and DLS
- Photophysical properties of novel ferrocenyl quinoline derivatives with red emission in solutions and polymeric matrices
- Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
- ArF laser photolytic deposition and thermal modification of an ultrafine chlorohydrocarbon
- Asymmetric synthesis of machilin C and its analogue
- Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents
- Single crystal X-ray structure and optical properties of anthraquinone-based dyes
- Low-density polyethylene in mixtures of hexane and benzene derivates
- Factors influencing aggregation behavior of poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in mixed solvents
- Chemical evaluation of Fallopia species leaves and antioxidant properties of their non-cellulosic polysaccharides
- Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues
- ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
Artikel in diesem Heft
- A deuterium-palladium electrode as a new sensor in non-aqueous solutions: potentiometric titration of weak acids in acetonitrile and benzonitrile
- Chemical variability of Artemisia herba-alba Asso essential oils from East Morocco
- Ag and Cu loaded on TiO2/graphite as a catalyst for Escherichia coli-contaminated water disinfection
- Direct electrochemistry and electrocatalysis of horseradish peroxidase immobilized in hyaluronic acid and single walled carbon nanotubes composite film
- Biological buffered saline solution as solvent in agar-carbomer hydrogel synthesis
- GC/MS analysis of gaseous degradation products formed during extrusion blow molding process of PE films
- Preparation, spectral, thermal, and biological properties of zinc(II) 4-chloro- and 5-chlorosalicylate complexes with methyl 3-pyridylcarbamate and phenazone
- Polyamidoamine dendrimer and dextran conjugates: preparation, characterization, and in vitro and in vivo evaluation
- Morphological characteristics of modified freeze-dried poly(N-isopropylacrylamide) microspheres studied by optical microscopy, SEM, and DLS
- Photophysical properties of novel ferrocenyl quinoline derivatives with red emission in solutions and polymeric matrices
- Preparation and characterization of hydrogels based on acryloyl end-capped four-arm star-shaped poly(ethylene glycol)-branched-oligo(l-lactide) via Michael-type addition reaction
- ArF laser photolytic deposition and thermal modification of an ultrafine chlorohydrocarbon
- Asymmetric synthesis of machilin C and its analogue
- Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents
- Single crystal X-ray structure and optical properties of anthraquinone-based dyes
- Low-density polyethylene in mixtures of hexane and benzene derivates
- Factors influencing aggregation behavior of poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in mixed solvents
- Chemical evaluation of Fallopia species leaves and antioxidant properties of their non-cellulosic polysaccharides
- Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues
- ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate
