Skip to main content
Log in

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

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

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

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Scheme 2

Similar content being viewed by others

References

  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

    Article  CAS  PubMed  Google Scholar 

  2. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, New York, p 30

    Google Scholar 

  3. Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100:1025–1074. https://doi.org/10.1021/cr940089p

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  6. Tietze LF (1996) Domino reactions in organic synthesis. Chem Rev 96:115–136. https://doi.org/10.1021/cr950027e

    Article  CAS  PubMed  Google Scholar 

  7. Pellissier H (2013) Stereocontrolled domino reactions. Chem Rev 113:442–524. https://doi.org/10.1021/cr300271k

    Article  CAS  PubMed  Google Scholar 

  8. Tietze LF, Brasche G, Gericke K (2006) Domino reactions in organic synthesis. Wiley, Weinheim. ISBN 3-527-29060-5

    Book  Google Scholar 

  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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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

    Article  CAS  Google Scholar 

  11. Zhu J, Bienaymé H (2005) Multicomponent reaction. Wiley, Weinheim. ISBN 978-3-527-30806-4

    Book  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  14. Roth HJ, Kleemann A (1988) Drug synthesis, in pharmaceutical chemistry, vol I. Wiley, New York. ISBN 0470210370

    Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  Google Scholar 

  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

    Article  Google Scholar 

  21. Groundwater PW, Solomons KR, Munawar AM (1996) Benzophenanthrolines and related fused acridines. Patent WO 1996018611 A2

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shanmugam Muthusubramanian.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1634 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Uma Maheswari, S., Vivek Kumar, S., Muthusubramanian, S. et al. A facile solvent-free three-component domino synthesis of novel 2,4-diaryl-5,6-dihydrobenzo[j][1,7]phenanthrolines. Mol Divers 23, 75–84 (2019). https://doi.org/10.1007/s11030-018-9847-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-018-9847-y

Keywords

Navigation