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Synthesis of Spiro[Indene-2,2′-Naphthalene]-4′-Carbonitriles and Spiro[Naphthalene-2,5′-Pyrimidine]-4-carbonitriles via One-pot Three Component Reaction Using Task Specific Ionic Liquid

  • Pooja Saluja
  • Garima Khanna
  • Ankita Chaudhary
  • Jitender M. Khurana
Conference paper

Abstract

A novel and efficient methodology has been developed for synthesizing indane-1,3-dione and pyrimidine based spirocyclic compounds. The synthesis has been achieved via multicomponent reaction of indane-1,3-dione/1.3-dimethylbarbituric acid, variously substituted aromatic aldehydes and cyclohexylidene malononitrile in presence of catalytic amount of TSIL [bmim]OH. Short reaction time, high yields and use of non-chromatographic purification techniques are some of the advantages of this methodology.

Keywords

Spiro compounds Ionic liquid MCRs Vinylogous Michael addition Knoevenagal condensation 

Notes

Acknowledgements

G.K. and P.S. thank CSIR, New Delhi and UGC, New Delhi, respectively, for providing financial assistance in form of junior and senior research fellowship.

Conflicts of Interest

Authors declare no conflict of interest.

References

  1. 1.
    (a) Formentἱn P, Garcἱa H, Leyva A (2004) Assessment of the suitability of imidazolium ionic liquids as reaction medium for base-catalysed reactions: case of Knoevenagel and Claisen–Schmidt reactions. J Mol Catal A: Chem 214:137–142.  https://doi.org/10.1016/j.molcata.2003.05.001; (b) Chen H, Justes DR, Cooks RG (2005) Proton affinities of N-heterocyclic carbene super bases. Org Lett 7:3949–3952.  https://doi.org/10.1021/ol0514247
  2. 2.
    Brindaban CR, Jana R, Sowmiah S (2007) An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid. J Org Chem 72:3152–3154.  https://doi.org/10.1021/jo070015gCrossRefGoogle Scholar
  3. 3.
    Yadav LDS, Singh S, Rai VK (2009) A one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins. Tetrahedron Lett 50:2208–2212.  https://doi.org/10.1016/j.tetlet.2009.02.166CrossRefGoogle Scholar
  4. 4.
    Xu J-M, Liu B-K, Wu W-B, Qian C, Wu Q, Lin XF (2006) Basic ionic liquid as catalysis and reaction medium: a novel and green protocol for the Markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH. J Org Chem 71:3991–3993.  https://doi.org/10.1021/jo0600914CrossRefPubMedGoogle Scholar
  5. 5.
    Wu H, Zhang F, Wan Y, Ye L (2008) An efficient protocol for henry reaction using basic ionic liquid [bmim]OH as catalyst and reaction medium. Lett Org Chem 5:209–211.  https://doi.org/10.2174/157017808783955817CrossRefGoogle Scholar
  6. 6.
    (a) Khurana JM, Chaudhary A (2012) Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem Lett Rev 5:633–638.  https://doi.org/10.1080/17518253.2012.691183; (b) Padvi SA, Tayade YA, Wagh YB, Dalal DS (2016) [bmim]OH: an efficient catalyst for the synthesis of mono and bis spirooxindole derivatives in ethanol at room temperature. Chin Chem Lett 27:714–720.  https://doi.org/10.1016/j.cclet.2016.01.016
  7. 7.
    Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89.  https://doi.org/10.1021/cr0505728CrossRefPubMedGoogle Scholar
  8. 8.
    Perron F, Albizati KF (1989) Chemistry of spiroketals. Chem Rev 89:1617–1661.  https://doi.org/10.1021/cr00097a015CrossRefGoogle Scholar
  9. 9.
    Knox C et al (2011) DrugBank 3.0: a comprehensive resource for ‘omics’ research on drugs. Nucleic Acids Res 39:D1035–D1041.  https://doi.org/10.1093/nar/gkq1126CrossRefPubMedGoogle Scholar
  10. 10.
    Khanna G, Chaudhary A, Khurana JM (2014) An efficient catalyst-free synthesis of novel benzo[a][1,3]oxazino[6,5-c]phenazine derivatives via one pot four-component domino protocol in water. Tetrahedron Lett 55:6652–6654.  https://doi.org/10.1016/j.tetlet.2014.10.067CrossRefGoogle Scholar
  11. 11.
    Khurana JM, Chaudhary A, Lumb A, Nand B (2012) An expedient four-component domino protocol for the synthesis of novel benzo[a]phenazine annulated heterocycles and their photophysical studies. Green Chem 14:2321.  https://doi.org/10.1039/C2GC35644ACrossRefGoogle Scholar
  12. 12.
    Khanna G, Aggarwal K, Khurana JM (2015) An efficient and confluent approach for the synthesis of novel 3,4-dihydro-2H-naphtho[2,3-e] [1,3]oxazine-5,10-dione derivatives by a three component reaction in ionic liquid. RSC Adv 5:46448–46454.  https://doi.org/10.1039/c5ra06169eCrossRefGoogle Scholar
  13. 13.
    Khanna G, Aggarwal K, Khurana JM (2016) Efficient catalyst-free synthesis of diversified bis(spirooxindoles) via one-pot, three-component reaction. Synth Commun 46:1880–1886.  https://doi.org/10.1080/00397911.2016.1233437CrossRefGoogle Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2018

Authors and Affiliations

  • Pooja Saluja
    • 1
  • Garima Khanna
    • 1
  • Ankita Chaudhary
    • 2
  • Jitender M. Khurana
    • 1
  1. 1.Department of ChemistryUniversity of DelhiDelhiIndia
  2. 2.Department of ChemistryMaitreyi CollegeChanakyapuri, New DelhiIndia

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