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A one-pot four-component domino protocol for the synthesis of indole and coumarin containing pyridine-3-carbonitrile derivatives

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Abstract

An efficient and simple protocol for the synthesis of a new class of diversely functionalized novel indole and coumarin containing pyridine-3-carbonitrile derivatives has been described through one-pot four-component condensation reaction of 3-(1H-indol-3-yl)-3-oxopropanenitrile, various aldehydes, 3-acetyl-2H-chromenones, and ammonium acetate in acetic acid conditions. The present new methodology offers several advantages such as short reaction time, easy experimental work-up, and good product yield, and endures the substrate diversity and operational simplicity under metal-free reaction conditions for the formation of C–C/C–N bonds.

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References

  1. Dömling A (2006) Chem Rev 106:17

    Article  CAS  PubMed  Google Scholar 

  2. Tu S, Jiang B, Zhang Y, Jia R, Zhang J, Yao C, Shi F (2007) Org Biomol Chem 5:355

    Article  CAS  PubMed  Google Scholar 

  3. Reddy CB, Kumar KS, Kumar MA, Narayana Reddy MV, Krishna BS, Naveen M, Arunasree MK, Reddy CS, Raju CN, Reddy CD (2012) Eur J Med Chem 47:553

    Article  CAS  PubMed  Google Scholar 

  4. Krishnammagari SK, Lee SM, Jeong YT (2018) Res Chem Intermed 44:517

    Article  CAS  Google Scholar 

  5. Krishnammagari SK, Cho BG, Jeong YT (2018) Phosphorus Sulfur Silicon Relat Elem 193:306

    Article  CAS  Google Scholar 

  6. Kumar KS, Krishna BS, Reddy CB, Reddy MVN, Reddy CS (2017) Arab J Chem 10:S368

    Article  CAS  Google Scholar 

  7. Wells JA, McClendon CL (2007) Nature 450:1001

    Article  CAS  PubMed  Google Scholar 

  8. Azzarito V, Long K, Murphy NS, Wilson AJ (2013) Nat Chem 5:161

    Article  CAS  PubMed  Google Scholar 

  9. Feng Y, Mitchison TJ, Bender A, Young DW, Tallarico JA (2009) Nat Rev Drug Discov 8:567

    Article  CAS  PubMed  Google Scholar 

  10. Humphrey GR, Kuethe JT (2006) Chem Rev 106:2875

    Article  CAS  PubMed  Google Scholar 

  11. Bandini M, Eichholzer A (2009) Angew Chem Int Ed 48:9608

    Article  CAS  Google Scholar 

  12. Kochanowska-Karamyan AJ, Hamann MT (2010) Chem Rev 110:4489

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Muthukumar A, Sekar G (2018) J Org Chem 83:8827

    Article  CAS  PubMed  Google Scholar 

  14. El-Sawy ER, Mandour AH, El-Hallouty SM, Shaker KH, Abo-Salem HM (2013) Arab J Chem 6:67

    Article  CAS  Google Scholar 

  15. Tu H, Wu SQ, Li XQ, Wan ZC, Wan JL, Tian K, Ouyang GP (2018) J Heterocycl Chem 55:269

    Article  CAS  Google Scholar 

  16. Franco LH, De Kier Joffé EB, Puricelli L, Tatian M, Seldes AM, Palermo JA (1998) J Nat Prod 61:1130

    Article  CAS  PubMed  Google Scholar 

  17. Zhu SL, Ji SJ, Zhao K, Liu Y (2008) Tetrahedron Lett 49:2578

    Article  CAS  Google Scholar 

  18. Teague SJ (2008) J Org Chem 73:9765

    Article  CAS  PubMed  Google Scholar 

  19. Bringmann G, Reichert Y, Kane VV (2004) Tetrahedron 60:3539

    Article  CAS  Google Scholar 

  20. Zhou Y, Kijima T, Kuwahara S, Watanabe M, Izumi T (2008) Tetrahedron Lett 49:3757

    Article  CAS  Google Scholar 

  21. Cooke MW, Hanan GS (2007) Chem Soc Rev 36:1466

    Article  CAS  PubMed  Google Scholar 

  22. Medina FG, Marrero JG, Macías-Alonso M, González MC, Córdova-Guerrero I, Teissier García AG, Osegueda-Robles S (2015) Nat Prod Rep 32:1472

    Article  CAS  PubMed  Google Scholar 

  23. Zhang RR, Liu J, Zhang Y, Hou MQ, Zhang MZ, Zhou F, Zhang WH (2016) Eur J Med Chem 116:76

    Article  CAS  PubMed  Google Scholar 

  24. Srikrishna D, Kumar Dubey P (2017) New J Chem 41:5168

    Article  CAS  Google Scholar 

  25. Danko M, Szabo E, Hrdlovic P (2011) Dyes Pigments 90:129

    Article  CAS  Google Scholar 

  26. Ghouili A, Dusek M, Petricek V, Ben Ayed T, Ben Hassen R (2014) J Phys Chem Solids 75:188

    Article  CAS  Google Scholar 

  27. Pereira TM, Vitório F, Amaral RC, Zanoni KPS, Murakami Iha NY, Kümmerle AE (2016) New J Chem 40:8846

    Article  CAS  Google Scholar 

  28. Sun Z, Wang Y, Fang D-C, Zhao Y (2018) New J Chem 42:7377

    Article  CAS  Google Scholar 

  29. Thirumurugan P, Perumal PT (2009) Tetrahedron 65:7620

    Article  CAS  Google Scholar 

  30. Shiri M, Zolfigol MA, Pirveysian M, Ayazi-Nasrabadi R, Kruger HG, Naicker T, Baltork IM (2012) Tetrahedron 68:6059

    Article  CAS  Google Scholar 

  31. Zhang F, Zhao Y, Sun L, Ding L, Gu Y, Gong P (2011) Eur J Med Chem 46:3149

    Article  CAS  PubMed  Google Scholar 

  32. Thirumurugan P, Nandakumar A, Muralidharan D, Perumal PT (2010) J Comb Chem 12:161

    Article  CAS  PubMed  Google Scholar 

  33. Zhao K, Xu X-P, Zhu S-L, Shi D-Q, Zhang Y, Ji S-J (2009) Synthesis 16:2697

    Google Scholar 

  34. Maleki A, Movahed H, Ravaghi P (2017) Carbohydr Polym 156:259

    Article  CAS  PubMed  Google Scholar 

  35. Vitório F, Pereira TM, Castro RN, Guedes GP, Graebin CS, Kümmerle AE (2015) New J Chem 39:2323

    Article  CAS  Google Scholar 

  36. Abouzid KAM, Al-Ansary GH, El-Naggar AM (2017) Eur J Med Chem 134:357

    Article  CAS  PubMed  Google Scholar 

  37. Krishnammagari SK, Jeong YT (2018) Res Chem Intermed 44:7311

    Article  CAS  Google Scholar 

  38. Jadhav AM, Krishnammagari SK, Kim JT, Jeong YT (2017) Tetrahedron 73:5163

    Article  CAS  Google Scholar 

  39. Balwe SG, Jeong YT (2018) Org Biomol Chem 16:1287

    Article  CAS  PubMed  Google Scholar 

  40. Balwe SG, Jeong YT (2018) Org Chem Front 5:1628

    Article  CAS  Google Scholar 

  41. Krishnammagari SK, Lim KT, Cho BG, Jeong YT (2018) Phosphorus Sulfur Silicon Relat Elem 193:574

    Article  CAS  Google Scholar 

  42. Evdokimov NM, Magedov IV, Kireev AS, Kornienko A (2006) Org Lett 5:899

    Article  CAS  Google Scholar 

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Acknowledgements

This research work was supported by the BK21 programme.

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Authors and Affiliations

  1. Department of Image Science and Engineering, Pukyong National University, Busan, 608-737, Republic of Korea

    Suresh Kumar Krishnammagari, Sandip Gangadhar Balwe, Jong Su Kim, Kwon Taek Lim & Yeon Tae Jeong

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  1. Suresh Kumar Krishnammagari
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  2. Sandip Gangadhar Balwe
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  3. Jong Su Kim
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  4. Kwon Taek Lim
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  5. Yeon Tae Jeong
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Corresponding author

Correspondence to Yeon Tae Jeong.

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Krishnammagari, S.K., Balwe, S.G., Kim, J.S. et al. A one-pot four-component domino protocol for the synthesis of indole and coumarin containing pyridine-3-carbonitrile derivatives. Monatsh Chem 150, 691–702 (2019). https://doi.org/10.1007/s00706-019-2365-5

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  • DOI: https://doi.org/10.1007/s00706-019-2365-5

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