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Facile synthesis of imidazo[1,2-a]pyridines promoted by room-temperature ionic liquids under ultrasound irradiation

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Abstract

A simple and efficient procedure for the synthesis of substituted imidazo[1,2-a]pyridines under ultrasound irradiation has been developed. The reactions were carried out using ionic liquids as catalyst. The reaction procedure demonstrated a broad substrate scope for both acetophenones and 2-aminopyridines, and provided convenient access to a wide variety of imidazo[1,2-a]pyridines. The present method offers several advantages compared to traditional heating methods such as higher yields, shorter reaction times, milder reaction conditions, and easier work-up procedure.

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References

  1. Gudmundsson KS, Williams JD, Drach JC, Townsend LB (2003) J Med Chem 46:1449

    Article  CAS  PubMed  Google Scholar 

  2. Gueiffier A, Mavel S, Lhassani M, Elhakmaoui A, Snoeck R, Andrei G, Chavignon O, Teulade JC, Witvrouw M, Balzarini J, De Clercq E, Chapat JP (1998) J Med Chem 41:5108

    Article  CAS  PubMed  Google Scholar 

  3. Lhassani M, Chavignon O, Chezal JM, Teulade JC, Chapat JP, Snoeck R, Andrei G, Balzarini J, De Clercq E, Gueiffier A (1999) Eur J Med Chem 34:271

    Article  CAS  Google Scholar 

  4. Chandra MD, Reddy DR, Nageswara RS, Adimurthy S (2013) Adv Synth Catal 355:2217

    Article  CAS  Google Scholar 

  5. Starrett JE, Montzka TA, Crosswell AR, Cavanagh RL (1989) J Med Chem 32:2204

    Article  CAS  PubMed  Google Scholar 

  6. Hieke M, Rödl CB, Wisniewska JM, la Buscató E, Stark H, Schubert-Zsilavecz M, Steinhilber D, Hofmann B, Proschak E (2012) Bioorg Med Chem Lett 22:1969

    Article  CAS  PubMed  Google Scholar 

  7. Hodgkiss RJ, Middleton RW, Parrick J, Rami HK, Wardman P, Wilson GD (1992) J Med Chem 35:1920

    Article  CAS  PubMed  Google Scholar 

  8. Donohoe TJ, Kabeshov MA, Rathi AH, Smith IED (2012) Org Biomol Chem 10:1093

    Article  CAS  PubMed  Google Scholar 

  9. Zeng J, Tan YJ, Leow ML, Liu X-W (2012) Org Lett 14:4386

    Article  CAS  PubMed  Google Scholar 

  10. Cao H, Liu X, Liao J, Huang J, Qiu H, Chen Q, Chen Y (2014) J Org Chem 79:11209

    Article  CAS  PubMed  Google Scholar 

  11. Bagdi AK, Rahman M, Santra S, Majee A, Hajra A (2013) Adv Synth Catal 355:1741

    Article  CAS  Google Scholar 

  12. Meng X, Wang Y, Yu C, Zhao P (2014) RSC Adv 4:27301

    Article  CAS  Google Scholar 

  13. Monir K, Bagdi AK, Ghosh M, Hajra A (2014) Org Lett 16:4630

    Article  CAS  PubMed  Google Scholar 

  14. Wang H, Wang Y, Liang D, Liu L, Zhang J, Zhu Q (2011) Angew Chem Int Ed 50:5678

    Article  CAS  Google Scholar 

  15. Chioua M, Soriano E, Infantes L, Jimeno ML, Marco-Contelles J, Samadi A (2013) Eur J Org Chem 2013:35

    Article  CAS  Google Scholar 

  16. Patil SV, Gaikwad ND, Bobade VD (2016) Arab J Chem 9:S1649

    Article  CAS  Google Scholar 

  17. Karade NN, Kondre JM, Gampawar SV, Shinde SV (2009) Synth Commun 39:2279

    Article  CAS  Google Scholar 

  18. Stasyuk AJ, Banasiewicz M, Cyrański MK, Gryko DT (2012) J Org Chem 77:5552

    Article  CAS  PubMed  Google Scholar 

  19. Kielesinski L, Tasior M, Gryko DT (2015) Org Chem Front 2:21

    Article  CAS  Google Scholar 

  20. Ranu BC, Jana R (2006) Eur J Org Chem 16:3767

    Article  CAS  Google Scholar 

  21. Wu X, Han X, Zhou L, Li A (2012) Indian J Chem 51A:791

    CAS  Google Scholar 

  22. Chakraborti AK, Roy SR, Kumar D, Chopra P (2008) Green Chem 10:1111

    Article  CAS  Google Scholar 

  23. Wasserscheid P, Eichmann M (2001) Catal Today 66:309

    Article  CAS  Google Scholar 

  24. Toma Š, Šebesta R (2012) Ionic liquids as (co-) solvents and co-catalysts for organocatalytic reactions. In: Ionic liquids in biotransformations and organocatalysis. Wiley, Hoboken, p 331

  25. Choi J, Benedetti TM, Jalili R, Walker A, Wallace GG, Officer DL (2016) Chem Eur J 22:14158

    Article  CAS  PubMed  Google Scholar 

  26. Palimkar SS, More VS, Srinivasan KV (2008) Ultrason Sonochem 15:853

    Article  CAS  PubMed  Google Scholar 

  27. Jin TS, Liu LB, Zhao Y, Li TS (2005) J Chem Res 3:162

    Article  Google Scholar 

  28. Mosslemin MH, Nateghi MR (2010) Ultrason Sonochem 17:162

    Article  CAS  PubMed  Google Scholar 

  29. Nikpassand M, Mamaghani M, Shirini F, Tabatabaeian K (2010) Ultrason Sonochem 17:301

    Article  CAS  PubMed  Google Scholar 

  30. Zou Y, Wu H, Hu Y, Liu H, Zhao X, Ji H, Shi D (2011) Ultrason Sonochem 18:708

    Article  CAS  PubMed  Google Scholar 

  31. Santra S, Bagdi AK, Majee A, Hajra A (2013) Adv Synth Catal 355:1065

    Article  CAS  Google Scholar 

  32. Yu J, Jin Y, Zhang H, Yang X, Fu H (2013) Chem Eur J 19:16804

    Article  CAS  PubMed  Google Scholar 

  33. Zhu DJ, Chen JX, Liu MC, Ding JC, Wu HY (2009) J Braz Chem Soc 20:482

    Article  CAS  Google Scholar 

  34. Adib M, Mohamadi A, Sheikhi E, Ansari S, Bijanzadeh HR (2010) Synlett 11:1606

    Article  CAS  Google Scholar 

  35. Xie YY, Chen ZC, Zheng QG (2002) Synthesis 11:1505

    Google Scholar 

  36. Ueno M, Togo H (2004) Synthesis 16:2673

    Google Scholar 

  37. Samanta S, Jana S, Mondal S, Monir K, Chandra SK, Hajra A (2016) Org Biomol Chem 14:5073

    Article  CAS  PubMed  Google Scholar 

  38. Kour D, Khajuria R, Kapoor KK (2016) Tetrahedron Lett 57:4464

    Article  CAS  Google Scholar 

  39. Mutai T, Tomoda H, Ohkawa T, Yabe Y, Araki K (2008) Angew Chem Int Ed 47:9522

    Article  CAS  Google Scholar 

  40. Sundberg RJ, Dahlhausen DJ, Manikumar G, Mavunkel B, Biswas A, Srinivasan V, King F, Waid P (1988) J Heterocycl Chem 2:129

    Article  Google Scholar 

  41. Wang FJ, Xu H, Xin M, Zhang Z (2016) Mol Divers 20:659

    Article  CAS  PubMed  Google Scholar 

  42. Habibi YA, Pourbasheer E, Danandeh JM (2008) Bull Korean Chem Soc 29:833

    Article  Google Scholar 

Download references

Acknowledgements

The first author would like to thank the Science Achievement Scholarship of Thailand for financial support. In addition, we wish to thank the Department of Chemistry, Faculty of Science, Chiang Mai University, Thailand, for facilities supporting this research.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

    Piyawat Paengphua & Sirirat Chancharunee

Authors
  1. Piyawat Paengphua
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  2. Sirirat Chancharunee
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Correspondence to Sirirat Chancharunee.

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Paengphua, P., Chancharunee, S. Facile synthesis of imidazo[1,2-a]pyridines promoted by room-temperature ionic liquids under ultrasound irradiation. Monatsh Chem 149, 1835–1840 (2018). https://doi.org/10.1007/s00706-018-2238-3

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  • DOI: https://doi.org/10.1007/s00706-018-2238-3

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