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A facile solvent-free three-component domino synthesis of novel 2,4-diaryl-5,6-dihydrobenzo[j][1,7]phenanthrolines

  • Shanmugavel Uma Maheswari
  • Sundaravel Vivek Kumar
  • Shanmugam Muthusubramanian
  • Subbu Perumal
Original Article
  • 89 Downloads

Abstract

A simple, efficient and green procedure for the synthesis of novel 2,4-diaryl-5,6-dihydrobenzo[j][1,7]phenanthrolines has been developed via a Krohnke-type one-pot three-component reaction of 2-[arylmethylidene]-3,4-dihydro-1(2H)-acridinones and (2-aryl-2-oxoethyl)pyridinium bromides in the presence of excess ammonium acetate in good yields under solvent-free conditions. Good functional group tolerance, high substrate scope and no column purification are the practical advantages of this methodology.

Graphical abstract

Keywords

Multicomponent domino reaction Solvent-free reaction Green chemistry Dihydrobenzo[j][1,7]phenanthrolines MCRs 

Notes

Acknowledgements

SM acknowledges the award of Emeritus Scientist Scheme from CSIR, New Delhi.

Supplementary material

11030_2018_9847_MOESM1_ESM.docx (1.6 mb)
Supplementary material 1 (DOCX 1634 kb)

References

  1. 1.
    Anastas PT, Kirchhoff MM (2002) Origins, current status, and future challenges of green chemistry. Acc Chem Res 35:686–694.  https://doi.org/10.1021/ar010065m CrossRefPubMedGoogle Scholar
  2. 2.
    Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, New York, p 30Google Scholar
  3. 3.
    Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100:1025–1074.  https://doi.org/10.1021/cr940089p CrossRefPubMedGoogle Scholar
  4. 4.
    Gawande MB, Bonifácio VDB, Luque R, Branco PS, Varma RS (2014) Solvent-free and catalysts-free chemistry: a benign pathway to sustainability. Chemsuschem 7:24–44.  https://doi.org/10.1002/cssc.201300485 CrossRefPubMedGoogle Scholar
  5. 5.
    Tietze LF, Modi A (2000) Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med Res Rev 20:304–322.  https://doi.org/10.1002/1098-1128(200007)20 CrossRefPubMedGoogle Scholar
  6. 6.
    Tietze LF (1996) Domino reactions in organic synthesis. Chem Rev 96:115–136.  https://doi.org/10.1021/cr950027e CrossRefPubMedGoogle Scholar
  7. 7.
    Pellissier H (2013) Stereocontrolled domino reactions. Chem Rev 113:442–524.  https://doi.org/10.1021/cr300271k CrossRefPubMedGoogle Scholar
  8. 8.
    Tietze LF, Brasche G, Gericke K (2006) Domino reactions in organic synthesis. Wiley, Weinheim. ISBN 3-527-29060-5CrossRefGoogle Scholar
  9. 9.
    Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112:3083–3135.  https://doi.org/10.1021/cr100233r CrossRefPubMedPubMedCentralGoogle Scholar
  10. 10.
    Ruijter E, Scheffelaar R, Orru RVA (2011) Multicomponent Reaction design in the quest for molecular complexity and diversity. Angew Chem Int Ed 50:6234–6246.  https://doi.org/10.1002/anie.201006515 CrossRefGoogle Scholar
  11. 11.
    Zhu J, Bienaymé H (2005) Multicomponent reaction. Wiley, Weinheim. ISBN 978-3-527-30806-4CrossRefGoogle Scholar
  12. 12.
    Singh MS, Chowdhury S (2012) Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis. RSC Adv 2:4547–4592.  https://doi.org/10.1039/C2RA01056A CrossRefGoogle Scholar
  13. 13.
    Kumar S, Bawa S, Gupta H (2009) Biological activities of quinoline derivatives. Mini Rev Med Chem 9:1648–1654.  https://doi.org/10.2174/138955709791012247 CrossRefPubMedGoogle Scholar
  14. 14.
    Roth HJ, Kleemann A (1988) Drug synthesis, in pharmaceutical chemistry, vol I. Wiley, New York. ISBN 0470210370Google Scholar
  15. 15.
    Schmitz FJ, DeGuzman FS, Hossain ME, van der Helm D (1991) Cytotoxic aromatic alkaloids from the ascidian Amphicarpa meridiana and Leptoclinides sp.: meridine and 11-hydroxyascididemin. J Org Chem 56:804–808.  https://doi.org/10.1021/jo00002a055 CrossRefGoogle Scholar
  16. 16.
    Delfourne E, Kiss R, Le Corre L, Dujols F, Bastide J, Collignon F, Lesur B, Frydman A, Darro F (2004) Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine. Bioorg Med Chem 12:3987–3994.  https://doi.org/10.1016/j.bmc.2004.06.006 CrossRefPubMedGoogle Scholar
  17. 17.
    Delfourne E, Darro F, Subielos NB, Decaestecker C, Bastide J, Frydman A, Kiss R (2001) Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid. J Med Chem 44:3275–3282.  https://doi.org/10.1021/jm0108496 CrossRefPubMedGoogle Scholar
  18. 18.
    Hu YZ, Zhang G, Thummel RP (2003) Friedländer approach for the incorporation of 6-bromoquinoline into novel chelating ligands. Org Lett 5:2251–2253.  https://doi.org/10.1021/ol034559q CrossRefPubMedGoogle Scholar
  19. 19.
    Cucciolito ME, Vitagliano A (1992) Selective stabilization of the anti isomer of (η3-allyl)palladium and -platinum complexes. Organometallics 11:3954–3964.  https://doi.org/10.1021/om00060a009 CrossRefGoogle Scholar
  20. 20.
    Albano G, Belser P, Cola LD, Gandolfi MT (1999) New luminescent ruthenium complexes with extended π systems. Chem Commun.  https://doi.org/10.1039/A900911F Google Scholar
  21. 21.
    Groundwater PW, Solomons KR, Munawar AM (1996) Benzophenanthrolines and related fused acridines. Patent WO 1996018611 A2Google Scholar
  22. 22.
    Roopan SM, Bharathi A, Palaniraja J, Anand K, Gengan RM (2015) Unexpected regiospecific Michael addition product: synthesis of 5,6-dihydrobenzo[1,7] phenanthrolines. RSC Adv 5:38640–38645.  https://doi.org/10.1039/C4RA16640J CrossRefGoogle Scholar
  23. 23.
    Vivek Kumar S, Muthusaravanan S, Muthusubramanian S, Perumal S (2016) An efficient one pot three-component domino reaction for the synthesis of 1,3,4-trisubstituted pyrroles. ChemistrySelect 1:675–679.  https://doi.org/10.1002/slct.201600108 CrossRefGoogle Scholar
  24. 24.
    Uma Rani G, Vivek Kumar S, Bharkavi C, Menendez JC, Perumal S (2016) One-pot access to a library of dispiro oxindole-pyrrolidine/pyrrolothiazole-thiochromane hybrids via three-component 1,3-dipolar cycloaddition reactions. ACS Comb Sci 18:337–342.  https://doi.org/10.1021/acscombsci.6b00011 CrossRefPubMedGoogle Scholar
  25. 25.
    Vivek Kumar S, Muthusubramanian S, Perumal S (2015) Facile “on water” domino reactions for the expedient synthesis of 2H-thiopyrano[2,3-b]quinolones. RSC Adv 5:30826–30832.  https://doi.org/10.1039/C5RA04795A CrossRefGoogle Scholar
  26. 26.
    Vivek Kumar S, Muthusubramanian S, Perumal S (2015) A solvent- and catalyst-free domino reaction for the efficient synthesis of 3-arylthiazolidine-2-thiones under microwave irradiation. RSC Adv 5:90451–90456.  https://doi.org/10.1039/C5RA19112B CrossRefGoogle Scholar
  27. 27.
    Vivek Kumar S, Muthusubramanian S, Menéndez JC, Perumal S (2015) An efficient synthesis of N-substituted 3-nitrothiophen-2-amines. Beilstein J Org Chem 11:1707–1712.  https://doi.org/10.3762/bjoc.11.185 CrossRefPubMedPubMedCentralGoogle Scholar
  28. 28.
    Prasanna P, Balamurugan K, Perumal S, Menéndez JC (2011) A facile, three-component domino protocol for the microwave-assisted synthesis of functionalized naphtho[2,3-b]furan-4,9-diones in water. Green Chem 13:2123–2129.  https://doi.org/10.1039/c0gc00952k CrossRefGoogle Scholar
  29. 29.
    Gunasekaran P, Balamurugan K, Sivakumar S, Perumal S, Menéndez JC, Almansour AI (2012) Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives. Green Chem 14:750–757.  https://doi.org/10.1039/c2gc16517a CrossRefGoogle Scholar
  30. 30.
    Indumathi S, Perumal S, Anbananthan N (2012) A facile eco-friendly three-component protocol for the regio- and stereoselective synthesis of functionalized trans-dihydrofuro[3,2-c]-quinolin-4(2H)-ones. Green Chem 14:3361–3367.  https://doi.org/10.1039/c2gc36040c CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  • Shanmugavel Uma Maheswari
    • 1
    • 2
  • Sundaravel Vivek Kumar
    • 1
  • Shanmugam Muthusubramanian
    • 1
  • Subbu Perumal
    • 1
  1. 1.Department of Organic Chemistry, School of ChemistryMadurai Kamaraj UniversityMaduraiIndia
  2. 2.Centre of Research and P.G. Studies in ChemistryAyya Nadar Janaki Ammal CollegeSivakasiIndia

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