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ZnAl2O4–Bi2O3 composite nano-powder as an efficient catalyst for the multi-component, one-pot, aqueous media preparation of novel 4H-chromene-3-carbonitriles

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Abstract

A composite structure of ZnAl2O4–Bi2O3 nanopowder was prepared from the reaction of a watery solution of Zn(NO3)2, Al(NO3)3, and Bi(NO3)3 with a dilute solution of amino ethanol in water via a simple precipitation-complexation method. The as-prepared composite was used for the one-pot synthesis of 2-amino-4-aryl-7-(pyrrolidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(piperidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-6-(2-(piperidin-1-yl)ethyl)-4H-chromene-3-carbonitrile and 2-amino-4-aryl-6-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile derivatives. This procedure is very simple and affords excellent yields.

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References

  1. T.C. McKee, R.W. Fuller, C.D. Covington, J.H.I.I. Cardellina, R.J. Gulakowski, B.L. Krepps, J.B. McMahon, M.R. Boyd, New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii. J. Nat. Prod. 59, 754–758 (1996)

    Article  CAS  Google Scholar 

  2. D.L. Galinis, R.W. Fuller, T.C. McKee, J.H.I.I. Cardellina, R.J. Gulakowski, J.B. McMahon, M.R. Boyd, Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (−)-calanolide B. J. Med. Chem. 39, 4507–4510 (1996)

    Article  CAS  Google Scholar 

  3. J.H.I.I. Cardellina, H.R. Bokesch, T.C. McKee, M.R. Boyd, Resolution and comparative anti-HIV evaluation of the enantiomers of calanolides A and B. Bioorg. Med. Chem. Lett. 5, 1011–1014 (1995)

    Article  CAS  Google Scholar 

  4. C. Garino, F. Bihel, N. Pietrancosta, Y. Laras, G. Quelever, I. Woo, P. Klein, J. Bain, J.-L. Boucher, J.-L. Kraus, New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones. Synthesis and biological properties. Bioorg. Med. Chem. Lett. 15, 135–138 (2005)

    Article  CAS  Google Scholar 

  5. G. Shanthi, P.T. Perumal, U. Rao, P.K. Sehgal, Synthesis and antioxidant activity of indolyl chromenes. Indian J. Chem. 48B, 1319–1323 (2009)

    CAS  Google Scholar 

  6. A.J. Johnson, R.A. Kumar, S.A. Rasheed, S.P. Chandrika, A. Chandrasekhar, S. Baby, A. Subramoniam, Antipyretic, analgesic, anti-inflammatory and antioxidant activities of two major chromenes from Melicope lunu-ankenda. J. Ethnopharmacol. 130, 267–271 (2010)

    Article  CAS  Google Scholar 

  7. S.X. Cai, J. Drewe, W. Kemnitzer, Discovery of 4-aryl-4H-chromenes as potent apoptosis inducers using a cell- and caspase-based Anti-cancer Screening Apoptosis Program (ASAP): SAR studies and the identification of novel vascular disrupting agents. Anticancer Agents Med. Chem. 9, 437–456 (2009)

    Article  CAS  Google Scholar 

  8. M.G. Dekamin, M. Eslami, A. Maleki, Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water. Tetrahedron 69, 1074–1085 (2013)

    Article  CAS  Google Scholar 

  9. S. Khaksar, A. Rouhollahpour, S.M. Talesh, A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium. J. Fluor. Chem. 141, 11–15 (2012)

    Article  CAS  Google Scholar 

  10. C. Lu, X.J. Huang, Y.Q. Li, M.Y. Zhou, W. Zheng, A one-pot multicomponent reaction for the synthesis of 2-amino-2-chromenes promoted by N, N-dimethylamino-functionalized basic ionic liquid catalysis under solvent-free condition. Monatsh. Chem. 140, 45–47 (2009)

    Article  Google Scholar 

  11. J. Safari, L. Javadian, Ultrasound assisted the green synthesis of 2-amino-4H-chromene derivatives catalyzed by Fe3O4-functionalized nanoparticles with chitosan as a novel and reusable magnetic catalyst. Ultrason. Sonochem. 22, 341–348 (2015)

    Article  CAS  Google Scholar 

  12. J. Safari, Z. Zarnegar, M. Heydarian, Practical, ecofriendly, and highly efficient synthesis of 2-amino-4H-chromenes using nanocrystalline MgO as a reusable heterogeneous catalyst in aqueous media. J. Taibah Univ. Sci. 7, 17–25 (2013)

    Article  Google Scholar 

  13. S.-L. Zhu, S.-J. Ji, Y. Zhang, A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium. Tetrahedron 63, 9365–9372 (2007)

    Article  CAS  Google Scholar 

  14. K. Pradhan, S. Paul, A.R. Das, Fe(DS)3, an efficient Lewis acid-surfactant-combined catalyst (LASC) for the one pot synthesis of chromeno[4,3-b]chromene derivatives by assembling the basic building blocks. Tetrahedron Lett. 54, 3105–3110 (2013)

    Article  CAS  Google Scholar 

  15. S. Paul, S. Ghosh, P. Bhattacharyya, A.R. Das, Synthesis of a SO3H-bearing carbonaceous solid catalyst, PEG–SAC: application for the easy access to a diversified library of pyran derivatives. RSC Adv. 3, 14254–14262 (2013)

    Article  CAS  Google Scholar 

  16. M.R.M. Shafiee, S.S. Mansoor, M. Ghashang, A. Fazlinia, Preparation of 3,4,5-substituted furan-2(5H)-ones using aluminum hydrogen sulfate as an efficient catalyst. Comptes Rendus Chimie 17, 131–134 (2014)

    Article  CAS  Google Scholar 

  17. M.R.M. Shafiee, R. Moloudi, M. Ghashang, Preparation of methyl (2-hydroxynaphthalen-1-yl)(aryl)methyl/benzylcarbamate derivatives using magnesium (II) 2,2,2-trifluoroacetate as an efficient catalyst. J. Chem. Res. 35, 622–625 (2011)

    Article  CAS  Google Scholar 

  18. M. Ghashang, Preparation and application of barium sulfate nano-particles in the synthesis of 2,4,5-triaryl and N-aryl(alkyl)-2,4,5-triaryl imidazoles. Curr. Org. Synth. 9, 727–732 (2012)

    Article  CAS  Google Scholar 

  19. M. Ghashang, Zinc hydrogen sulfate promoted multi-component preparation of highly functionalized piperidines. Lett. Org. Chem. 9, 497–502 (2012)

    Article  CAS  Google Scholar 

  20. M. Ghashang, S.S. Mansoor, K. Aswin, Poly(4-vinylpyridinium)hydrogen sulfate: a novel and efficient catalyst for the synthesis of 13-Aryl-indeno[1,2-b]naphtha[1,2-e]pyran-12(13H)-ones under solvent-free conditions. Chin. J. Catal. 35, 43 (2014)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are indebted to the Islamic Azad University, Najafabad Branch for financial support of this research.

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  1. Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, P.O. Box 517, Najafabad, Esfahān, Iran

    Majid Ghashang

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  1. Majid Ghashang
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Correspondence to Majid Ghashang.

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Ghashang, M. ZnAl2O4–Bi2O3 composite nano-powder as an efficient catalyst for the multi-component, one-pot, aqueous media preparation of novel 4H-chromene-3-carbonitriles. Res Chem Intermed 42, 4191–4205 (2016). https://doi.org/10.1007/s11164-015-2269-x

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