Skip to main content
Log in

Vanadium dodecylamino phosphate: A novel efficient catalyst for synthesis of polyhydroquinolines

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

A novel vanadium dodecylamino phosphate was synthesised by an instant reaction between phosphoric acid and vanadyl acetylacetonoate using dodecylamine as the structure-directing agent at ambient temperature. The physicochemical characteristics of the material were investigated by a variety of analytical techniques. XRD studies revealed the presence of vanadium phosphate and hydrated vanadium phosphate phases in the framework of the material. The catalytic application of this material toward in the synthesis of polyhydroquinolines via Hantzsch condensation was investigated at ambient temperature. This method affords high yields within short reaction times. The influence of various reaction parameters such as different solvents, catalyst dosage, effect of aldehydes, and reusability was studied and a plausible mechanism proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Beneš, L., Melánová, K., Zima, V., Trchová, M., Čapková, P., & Koudelka, B. (2006). Vanadyl phosphate intercalated with dimethyl sulfoxide. Journal of Physics and Chemistry of Solids, 67, 956–960. DOI:10.1016/j.jpcs.2006.01.009.

    Article  Google Scholar 

  • Bergman, R. L., & Frisch, N. W. (1966). U.S. Patent No. 3293268. Washington, DC, USA: U.S. Patent and Trademark Office.

  • Borah, P.,& Datta, A. (2010). Exfoliated VOPO4 · 2H2O dispersed on alumina as a novel catalyst for the selective oxidation of cyclohexane. Applied Catalysis A: General, 376, 19–24. DOI:10.1016/j.apcata.2009.11.020.

    Article  CAS  Google Scholar 

  • Cavani, F., Foresti, E., Trifiró, F.,& Busca, G. (1987). Nature of active species in the ammoxidation of toluene over V2O5/TiO2 catalysts prepared by flash-drying. Journal of Catalysis, 106(1), 251–262. DOI: 10.1016/0021-9517(87) 90229-6.

    Article  CAS  Google Scholar 

  • Chandrasekhar, S., Rao, Y. S., Sreelakshmi, L., Mahipal, B.,& Reddy, C. R. (2008). Tris(pentafluorophenyl)boranecatalyzed three-component reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions. Synthesis, 2008, 1737–1740. DOI:10.1055/s-2008-1067039.

    Article  Google Scholar 

  • Chen, Y. L., Fang, K. C., Sheu, J. Y., Hsu, S. L.,& Tzeng, C. C. (2001). Synthesis and antibacterial evaluation of certain quinolone derivatives. Journal of Medicinal Chemistry, 44, 2374–2377. DOI: 10.1021/jm0100335.

    Article  CAS  Google Scholar 

  • Chen, W. Y., Qin, S. D.,& Jin, J. R. (2007). HBF4-catalyzed Biginelli reaction: One-pot synthesis of dihydropyrimidin-2(1H)-ones under solvent-free conditions. Catalysis Communications, 8, 123–126. DOI:10.1016/j.catcom.2006.05.026.

    Article  CAS  Google Scholar 

  • Choudary, B. M., Neeraja, V.,& Lakshmi Kantam, M. (2001). Vanadyl(IV) acetate: a mild and efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols, thiols and phenols. Journal of Molecular Catalysis A: Chemical, 175, 169–172. DOI: 10.1016/s1381-1169(01)00202-3.

    Article  CAS  Google Scholar 

  • Das, B., Ravikanth, B., Ramu, R.,& Rao, B. V. (2006). An efficient one-pot synthesis of polyhydroquinolines at room temperature using HY-zeolite. Chemical & Pharmaceutical Bulletin, 54, 1044–1045. DOI: 10.1248/cpb.54.1044.

    Article  CAS  Google Scholar 

  • Das, D. P.,& Parida, K. M. (2008). Solar light induced photocatalytic degradation of pollutants over titania pillared zirconium phosphate and titanium phosphate. Catalysis Surveys from Asia, 12, 203–213. DOI: 10.1007/s10563-008-9052-6.

    Article  CAS  Google Scholar 

  • Dasgupta, S., Agarwal, M.,& Datta, A. (2002). Long chain alkyl amine templated synthesis of a mesostructured lamellar vanadium phosphate phase. Journal of Materials Chemistry, 12, 162–164. DOI: 10.1039/b109472f.

    Article  CAS  Google Scholar 

  • Dasgupta, S., Agarwal, M.,& Datta, A. (2004). Surfactant assisted organization of an exfoliated vanadyl ortho phosphate to a mesostructured lamellar vanadium phosphate phase. Microporous and Mesoporous Materials, 67, 229–234. DOI:10.1016/j.micromeso.2003.11.006.

    Article  CAS  Google Scholar 

  • Datta, A., Dasgupta, S., Agarwal, M.,& Ray, S. S. (2005). Mesolamellar VPO phases obtained by incorporating long chain alkyl amine surfactants into the layered vanadium phosphate dihydrate phase. Microporous and Mesoporous Materials, 83, 114–124. DOI:10.1016/j.micromeso.2005.03.019.

    Article  CAS  Google Scholar 

  • Dias, C. R., Portela, M. F., Galán-Fereres, M., Bañares, M. A., López Granados, M., Peña, M. A.,& Fierro, J. L. G. (1997). Selective oxidation of o-xylene to phthalic anhydride on V2O5 supported on TiO2-coated SiO2. Catalysis Letters, 43, 117–121. DOI:10.1023/a:1018990506391.

    Article  CAS  Google Scholar 

  • Evans, C. G.,& Gestwicki, J. E. (2009). Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines. Organic Letters, 11, 2957–2959. DOI: 10.1021/ol901114f.

    Article  CAS  Google Scholar 

  • Gribot-Perrin, N., Volta, J. C., Burrows, A., Kiely, C.,& Gubelmann-Bonneau, M. (1996). On the role of microstructure of vanadium phosphorus oxides for propane oxidation to acrylic acid. Studies in Surface Science and Catalysis, 101, 1205–1214. DOI: 10.1016/s0167-2991(96)80332-6.

    Article  CAS  Google Scholar 

  • Guan, J. Q., Xu, H. Y., Jing, S. B., Wu, S. J., Ma, Y. Y., Shao, Y. Q.,& Kan, Q. B. (2008). Selective oxidation of isobutane and isobutene over vanadium phosphorus oxides. Catalysis Communications, 10, 276–280. DOI:10.1016/j.catcom.2008.09.003.

    Article  CAS  Google Scholar 

  • Guliants, V. V., Benziger, J. B., Sundaresan, S., Wachs, I. E., Jehng, J. M.,& Roberts, J. E. (1996). The effect of the phase composition of model VPO catalysts for partial oxidation of n-butane. Catalysis Today, 28, 275–295. DOI: 10.1016/s0920-5861(96)00043-0.

    Article  CAS  Google Scholar 

  • Heydari, A., Khaksar, S., Tajbakhsh, M.,& Bijanzadeh, H. R. (2009). One-step synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols. Journal of Fluorine Chemistry, 130, 609–614. DOI:10.1016/j.jfluchem.2009.03.014.

    Article  CAS  Google Scholar 

  • Hong, M., Cai, C., & Yi, W. B. (2010). Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium. Journal of Fluorine Chemistry, 131, 111–114. DOI:10.1016/j.jfluchem.2009.10.009.

    Article  CAS  Google Scholar 

  • Ji, S. J., Jiang, Z. Q., Lu, J.,& Loh, T. P. (2004). Facile ionic liquids-promoted one-pot synthesis of polyhydroquinoline derivatives under solvent-free conditions. Synlett, 2004, 831–835. DOI:10.1055/s-2004-820035.

    Article  Google Scholar 

  • Ko, S. K., Sastry, M. N. V., Lin, C. C.,& Yao, C. F. (2005). Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction. Tetrahedron Letters, 46, 5771–5774. DOI: 10.1016/j.tetlet.2005.05.148.

    Article  CAS  Google Scholar 

  • Kondratenko, E. V., Cherian, M.,& Baerns, M. (2006). Oxidative dehydrogenation of propane over differently structured vanadia-based catalysts in the presence of O2 and N2O. Catalysis Today, 112, 60–63. DOI:10.1016/j.cattod.2005.11.028.

    Article  CAS  Google Scholar 

  • Kolvari, E., Zolfigol, M. A., Koukabi, N.,& Shirmardi-Shaghasemi, B. (2011). A simple and efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines using silica sulphuric acid as a heterogeneous and reusable catalyst under solvent-free conditions. Chemical Papers, 65, 898–902. DOI: 10.2478/s11696-011-0087-1.

    Article  CAS  Google Scholar 

  • Kumar, S., Sharma, P., Kapoor, K. K.,& Hundal, M. S. (2008). An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding. Tetrahedron, 64, 536–542. DOI:10.1016/j.tet.2007.11.008.

    Article  CAS  Google Scholar 

  • Machado, M. O., de Farias, R. F.,& Airoldi, C. (2004). Two different synthetic routes involving the reaction of dodecylamine or nicotinamide with crystalline lamellar vanadylphosphate. Journal of Physics and Chemistry of Solids, 65, 1697–1703. DOI:10.1016/j.jpcs.2004.04.008.

    Article  CAS  Google Scholar 

  • Nagaraju, P., Lingaiah, N., Prasad, P. S. S., Kalevaru, V. N.,& Martin, A. (2008). Preparation, characterization and catalytic properties of promoted vanadium phosphate catalysts. Catalysis Communications, 9, 2449–2454. DOI:10.1016/j.catcom.2008.06.012.

    Article  CAS  Google Scholar 

  • Nagarapu, L., Apuri, S., Gaddam, S., Bantu, R., Mahankhali, V. C.,& Kantevari, S. (2008). A facile synthesis of polyhydroquinoline derivatives via the Hantzsch reaction under solvent free-conditions using potassium dodecatungsto cobaltate trihydrate (K5CoW12O40.3H2O). Letters in Organic Chemistry, 5, 60–64. DOI: 10.2174/157017808783330162.

    Article  CAS  Google Scholar 

  • Nguyen-Phan, T. D., Song, M. B., Yun, H., R. Kim, E. J., Oh, E. S.,& Shin, E. W. (2011). Characterization of vanadiumdoped mesoporous titania and its adsorption of gaseous benzene. Applied Surface Science, 257, 2024–2031. DOI:10.1016/j.apsusc.2010.09.046.

    Article  CAS  Google Scholar 

  • Oskooie, H. A., Baghernezhad, B., Heravi M. M.,& Beheshtiha, Y. Sh. (2008). Vanadyl sulfate (VOSO4.3H2O). An efficient catalyst for acylation of alcohols and phenols under solvent free condition. Journal of the Chinese Chemical Society, 55, 713–715.

    CAS  Google Scholar 

  • Perozo-Rondón, E., Calvino-Casilda, V., Martín-Aranda, R. M., Casal, B., Durán-Valle, C. J.,& Rojas-Cervantes, M. L. (2006). Catalysis by basic carbons: Preparation of dihydropyridines. Applied Surface Science, 252, 6080–6083. DOI:10.1016/j.apsusc.2005.11.017.

    Article  Google Scholar 

  • Rownaghi, A. A., Taufiq-Yap, Y. H.,& Rezaei, F. (2009). Solvothermal synthesis of vanadium phosphate catalysts for n-butane oxidation. Journal of Chemical Engineering, 155, 514–522. DOI:10.1016/j.cej.2009.07.055.

    Article  CAS  Google Scholar 

  • Sabitha, G., Kiran Kumar Reddy, G. S., Srinavas Reddy, C.,& Yadav, J. S. (2003a). A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature. Tetrahedron Letters, 44, 4129–4131. DOI: 10.1016/s0040-4039(03)00813-x.

    Article  CAS  Google Scholar 

  • Sabitha, G., Kiran Kumar Reddy, G. S., Bhaskar Reddy, K.,& Yadav, J. S. (2003b). Vanadium(III) chloride catalyzed Biginelli condensation: solution phase library generation of dihydropyrimidin-(2H)-ones. Tetrahedron Letters, 44, 6497–6499. DOI: 10.1016/s0040-4039(03)01564-8.

    Article  CAS  Google Scholar 

  • Samantaray, S. K., Mishra, T.,& Parida, K. M. (2000). Studies on anion promoted titania: 2: Preparation, characterisation and catalytic activity towards aromatic alkylation over sulfated titania. Journal of Molecular Catalysis A: Chemical, 156, 267–274. DOI: 10.1016/s1381-1169(99)00424-0.

    Article  CAS  Google Scholar 

  • Shan, R. D., Velazquez, C.,& Knaus, E. E. (2004). Syntheses, calcium channel agonist-antagonist modulation activities, and nitric oxide release studies of nitrooxyalkyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2,1,3-benzoxadiazol-4-yl)pyridine-5-carboxylate racemates, enantiomers, and diastereomers. Journal of Medicinal Chemistry, 47, 254–261. DOI: 10.1021/jm030333h.

    Article  CAS  Google Scholar 

  • Solsona, B., Zazhigalov, V. A., López-Nieto, J. M., Bacherikova, I. V.,& Diyuk, E. A. (2003). Oxidative dehydrogenation of ethane on promoted VPO catalysts. Applied Catalysis A: General, 249, 81–92. DOI: 10.1016/s0926-860x(03)00178-9.

    Article  CAS  Google Scholar 

  • Song, G. Y., Wang, B., Wu, X. Y., Kang, Y. R.,& Yang, L. M. (2005). Montmorillonite K10 clay: An effective solid catalyst for one-pot synthesis of polyhydroquinoline derivatives. Synthetic Communications, 35, 2875–2880. DOI: 10.1080/00397910500297255.

    Article  CAS  Google Scholar 

  • Sunil Kumar, B., Kumar, P. S., Srinivasulu, N., Rajitha, B., Thirupathi Reddy, Y., Narsimha Reddy, P., & Udupi, R. H. (2006). Vanadium(III) chloride as an effective catalyst for the Pechmann reaction. Chemistry of Heterocyclic Compounds, 42, 172–175. DOI: 10.1007/s10593-006-0066-6.

    Article  Google Scholar 

  • Venkatathri, N., Santhanaraj, D.,& Shanthi, K. (2008). Synthesis, characterization and catalytic properties of a novel Mn — organophosphate having MFI topology. Bulletin of the Catalysis Society of India, 7(3), 97–104.

    Google Scholar 

  • Wang, L. M., Sheng, J., Zhang, L., Han, J. W., Fan, Z. Y., Tian, H.,& Qian, C. T. (2005). Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction. Tetrahedron, 61, 1539–1543. DOI:10.1016/j.tet.2004.11.079.

    Article  CAS  Google Scholar 

  • Wang, C. T., Chen, M. T.,& Lai, D. L. (2011). Surface characterization and reactivity of vanadium-tin oxide nanoparticles. Applied Surface Science, 257, 5109–5114. DOI:10.1016/j.apsusc.2011.01.031.

    Article  CAS  Google Scholar 

  • Whittington, B. I.,& Anderson, J. R. (1993). Nature and activity of some vanadium catalysts. The Journal of Physical Chemistry, 97, 1032–1041. DOI: 10.1021/j100107a010.

    Article  CAS  Google Scholar 

  • Wu, Z. L., Dai, S.,& Overbury, S. H. (2010). Multiwavelength Raman spectroscopic study of silica-supported vanadium oxide catalysts. The Journal of Physical Chemistry C, 114, 412–422. DOI: 10.1021/jp9084876.

    Article  CAS  Google Scholar 

  • Xue, M. W., Chen, H., Zhang, H. L., Auroux, A.,& Shen, J. Y. (2010). Preparation and characterization of V-Ag-O catalysts for the selective oxidation of toluene. Applied Catalysis A: General, 379, 7–14. DOI:10.1016/j.apcata.2010.02.023.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Venkatathri Narayanan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rajini, A., Nookaraju, M., Reddy, I.A.K. et al. Vanadium dodecylamino phosphate: A novel efficient catalyst for synthesis of polyhydroquinolines. Chem. Pap. 68, 170–179 (2014). https://doi.org/10.2478/s11696-013-0441-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-013-0441-6

Keywords

Navigation