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Syntheses of quinolines and their derivatives from α,β-unsaturated aldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

The methods for the synthesis of quinoline and its hydrogenated derivatives from α,β-unsaturated aldehydes have been summarized for the first time. The review highlights the advances in this area over the past 15 years. Particular attention is focused on the use of catalytic systems, synthetic advantages, and mechanistic aspects of the reactions.

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References

  1. Matada, B. S.; Pattanashettar, R.; Yernale, N. G. Bioorg. Med. Chem. 2021, 32, 115973.

  2. Kumar, L.; Salahuddin; Mazumder, A.; Pandey, D.; Yar, M. S.; Kumar, R.; Mazumder, R.; Sarafroz, M.; Ahsan, M. J.; Kumar, V.; Gupta, S. Mini-Rev. Org. Chem. 2019, 16, 653.

  3. Nainwal, L. M.; Tasneem, S.; Akhtar, W.; Verma, G.; Khan, M. F.; Parvez, S.; Shaquiquzzaman, M.; Akhter, M.; Alam, M. M. Eur. J. Med. Chem., 2019, 164, 121.

    Article  CAS  PubMed  Google Scholar 

  4. Upadhayaya, R. S.; Vandavasi, J. K.; Vasireddy, N. R.; Sharma, V.; Dixit, S. S.; Chattopadhyaya, J. Bioorg. Med. Chem. 2009, 17, 2830.

    Article  CAS  PubMed  Google Scholar 

  5. Chen, S.; Chen, R.; He, M.; Pang, R.; Tan, Z.; Yang, M. Bioorg. Med. Chem. 2009, 17, 1948.

    Google Scholar 

  6. Sun, N.; Du, R.-L.; Zheng, Y.-Y.; Huang, B.-H.; Guo, Q.; Zhang, R.-F.; Wong, K.-Y.; Lu, Y.-J. Eur. J. Med. Chem. 2017, 135, 1.

    Article  CAS  PubMed  Google Scholar 

  7. Pinz, M. P.; Reis, A. S.; Leivas de Oliveira, R.; Voss, G. T.; Vogt, A. G.; do Sacramento, M.; Roehrs, J. A.; Alves, D.; Luchese, C.; Wilhelm, E. A. Regul. Toxicol. Pharmacol. 2017, 90, 72.

  8. Keri, R. S.; Patil, S. A. Biomed. Pharmacother. 2014, 68, 1161.

    Article  CAS  PubMed  Google Scholar 

  9. Solomon, V. R.; Lee, H. Curr. Med. Chem. 2011, 18, 1488.

    Article  CAS  PubMed  Google Scholar 

  10. Nothdurft, H. D.; Kain, K. C. In The Travel and Tropical Medicine Manual; Sanford, C. A.; Pottinger, P. S.; Jong, E. C., Eds.; Elsevier: Edinburgh, 2017, 5th ed., p. 71.

  11. Krafts, K.; Hempelmann, E.; Skórska-Stania, A. Parasitol. Res. 2012, 111, 1.

    Article  PubMed  Google Scholar 

  12. del Río-Rodríguez, R.; Fragoso-Jarillo, L.; Garrido-Castro, A. F.; Maestro, M. C.; Fernández-Salas, J. A.; Alemán, J. Chem. Sci. 2022, 13, 6512.

  13. Sharique, M.; Majhi, J.; Dhungana, R. K.; Kammer, L. M.; Krumb, M.; Lipp, A.; Romero, E.; Molander, G. A. Chem. Sci. 2022, 13, 5701.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Wang, D.; Zhang, L.; Xiao, F.; Mao, G.; Deng, G.-J.; Org. Chem. Front. 2022, 9, 2986.

    Article  CAS  Google Scholar 

  15. Sugiura, M.; Yamaguchi, N.; Saya, T.; Ito, M.; Asai, K.; Maeba, I. Tetrahedron Lett. 2002, 43, 5295.

    Article  CAS  Google Scholar 

  16. Avetisyan, A. A.; Aleksanyan, I. L.; Ambartsumyan, L. P. Russ. J. Org. Chem. 2005, 41, 772.

    Article  CAS  Google Scholar 

  17. Muthukrishnan, I.; Sridharan, V.; Menéndez, J. C. Chem. Rev. 2019, 119, 5057.

    Article  CAS  PubMed  Google Scholar 

  18. Xuan, D. D. Curr. Org. Synth. 2019, 16, 671.

    Article  CAS  PubMed  Google Scholar 

  19. Harry, N. A.; Ujwaldev, S. M.; Anilkumar, G. Org. Biomol. Chem. 2020, 18, 9775.

    Article  CAS  PubMed  Google Scholar 

  20. Dhiya, A. K.; Monga, A.; Sharma, A. Org. Chem. Front. 2021, 8, 1657.

    Article  CAS  Google Scholar 

  21. Dhayalan, V.; Dandela, R.; Devi, K. B.; Dhanusuraman, R. SynOpen 2022, 06, 31.

    Article  CAS  Google Scholar 

  22. Abass, M.; Hassanin, H. M.; Allimony, H. A.; Hassan, H. Chem. Heterocycl. Compd. 2015, 51, 1023.

    Article  CAS  Google Scholar 

  23. Zagorska, P. A.; Grigorjeva, L.; Bolsakova, J. Chem. Heterocycl. Compd. 2021, 57, 159.

  24. Keiko, N. A.; Vchislo, N. V. Chem. Heterocycl. Compd. 2016, 52, 222.

    Article  CAS  Google Scholar 

  25. Keiko, N. A.; Vchislo, N. V. Asian J. Org. Chem. 2016, 5, 439.

  26. Keiko, N. A.; Vchislo, N. V. Asian J. Org. Chem. 2016, 5, 1169.

  27. Vchislo, N. V.; Verochkina, E. A. Chem. Heterocycl. Compd. 2019, 55, 598.

    Article  CAS  Google Scholar 

  28. Vchislo, N. V. Asian J. Org. Chem. 2019, 8, 1207.

  29. Vchislo, N. V. Mini-Rev. Org. Chem. 2017, 14, 197.

    Article  CAS  Google Scholar 

  30. Vchislo, N. V.; Verochkina, E. A. ChemistrySelect 2020, 5, 9579.

    Article  CAS  Google Scholar 

  31. Weyesa, A.; Mulugeta, E. RSC Adv. 2020, 10, 20784.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Sivaprasad, G.; Rajesh, R.; Perumal, P. T. Tetrahedron Lett. 2006, 47, 1783.

    Article  CAS  Google Scholar 

  33. Paolis, O. D.; Teixera, L.; Török, B. Tetrahedron Lett. 2009, 50, 2939.

    Article  Google Scholar 

  34. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301.

    Article  CAS  PubMed  Google Scholar 

  35. Reynolds, K. A.; Young, D. J.; Loughlin, W. A. Synthesis 2010, 3645.

  36. Yalgin, H.; Luart, D.; Len, C. J. Flow Chem. 2016, 6, 80.

  37. Ivanković, A.; Dronjić, A.; Martinović Bevanda, A.; Talić, S. Int. J. Sustainable Green Energy 2017, 6, 39.

    Article  Google Scholar 

  38. Zhang, X.; Xu, X. Chem. Asian J. 2014, 9, 3089.

    Article  CAS  PubMed  Google Scholar 

  39. Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. Pure Appl. Chem. 2003, 75, 29.

    Article  CAS  Google Scholar 

  40. Сameron, M.; Hoerrner, R. S.; McNamara, J. M.; Figus, M.; Thomas, S. Org. Process Res. Dev. 2006, 10, 149.

    Article  Google Scholar 

  41. Li, J.; Kung, D. W.; Griffith, D. A. Tetrahedron Lett. 2010, 51, 3876.

    Article  CAS  Google Scholar 

  42. Xing, R.-G.; Li, Y.-N.; Liu, Q.; Han, Y.-F.; Wei, X.; Li, J.; Zhou, B. Synthesis 2011, 2066.

  43. Rodrigo, E.; Baunis, H.; Suna, E.; Waldvogel, S. R. Chem. Commun. 2019, 55, 12255.

    Article  CAS  Google Scholar 

  44. Gao, Y.; Yang, S.; Huo, Y.; Chen, Q.; Li, X.; Hu, X.-Q. ACS Catal. 2021, 11, 7772.

    Article  CAS  Google Scholar 

  45. Mäkelä, M. K.; Bulatov, E.; Malinen, K.; Talvitie, J.; Nieger, M.; Melchionna, M.; Anna, L.; Hu, T.; Wirtanen, T.; Helaja, J. Adv. Synth. Catal. 2021, 363, 3775.

    Article  Google Scholar 

  46. Aukland, M. H.; List, B. Pure Appl. Chem. 2021, 93, 1371.

    Article  CAS  Google Scholar 

  47. Zhou, H.; Zhou, Y.; Bae, H. Y.; Leutzsch, M.; Li, Y.; De, C. K.; Cheng, G.-J.; List, B. Nature 2022, 605, 84. https://doi.org/10.1038/s41586-022-04531-5

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Hargittai, I. Struct. Chem. 2022, 33, 303.

    Article  CAS  Google Scholar 

  49. Zhang, X.; Song, X.; Li, H.; Zhang, S.; Chen, X.; Yu, X.; Wang, W. Angew. Chem., Int. Ed. 2012, 51, 7282.

    Article  CAS  Google Scholar 

  50. Lee, Y.; Heo, S.; Kim, S.-G. Adv. Synth. Catal. 2015, 357, 1545.

    Article  CAS  Google Scholar 

  51. Wang, J.; Rong, Q.; Zhao, L.; Pan, X.; Zhao, L.; Zhao, K.; Hu, L. J. Org. Chem. 2020, 85, 11240.

    Article  CAS  PubMed  Google Scholar 

  52. Shao, Y.-D.; Han, D.-D.; Dong, M.-M.; Yang, X.-R.; Cheng, D. J. Org. Chem. Front. 2021, 8, 605.

    Article  CAS  Google Scholar 

  53. Zhang, J.; Xu, Y.; Wang, Z.; Zhong, R.; Wang, Y. J. Org. Chem. 2021, 86, 4262.

    Article  CAS  PubMed  Google Scholar 

  54. Yang, G.; Sun, S.; Li, Z.; Liu, Y.; Wang, J. Commun. Chem. 2021, 4, 144.

    Article  CAS  Google Scholar 

  55. Dutt, S.; Tyagi, V. Tetrahedron Lett. 2021, 87, 153527.

    Article  CAS  Google Scholar 

  56. Jacquemond-Collet, I.; Benoit-Vical, F.; Mustofa; Valentin, A.; Stanislas, E.; Mallié, M.; Fourasté, I. Planta Med. 2002, 68, 68.

  57. Kosmas, C. E.; DeJesus, E.; Rosario, D.; Vittorio, T. J. Clin. Med. Insights: Cardiol. 2016, 10, 37.

    CAS  Google Scholar 

  58. Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111, 7157.

    Article  CAS  PubMed  Google Scholar 

  59. Fustero, S.; Moscardó, J.; Jiménez, D.; Pérez-Carrión, M. D.; Sánchez-Roselló, M.; del Pozo, C. Chem.–Eur. J. 2008, 14, 9868.

  60. Lu, H.-H.; Liu, H.; Wu, W.; Wang, X.-F.; Lu, L.-Q.; Xiao, W.-J. Chem.–Eur. J. 2009, 15, 2742.

  61. Quin, L. D.; Tyrell, J. A. Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals; J. Wiley&Sons: Hoboken, 2010, p. 112.

  62. Bryant, L. A.; Shankland, K.; Straker, H. E.; Johnston, C. D.; Lees, N. R.; Cobb, A. J. A. Adv. Synth. Catal. 2021, 363, 4067.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. Sridharan, V.; Avendaňo, C.; Menéndez, J. C. Tetrahedron 2009, 65, 2087.

    Article  CAS  Google Scholar 

  64. Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598.

    Article  CAS  PubMed  Google Scholar 

  65. Dagousset, G.; Zhu, J.; Masson, G. J. Am. Chem. Soc. 2011, 133, 14804.

    Article  CAS  PubMed  Google Scholar 

  66. Heo, S.; Kim, S.; Kim, S.-G. Tetrahedron Lett. 2013, 54, 4978.

    Article  CAS  Google Scholar 

  67. Kim, C.; Kim, S.-G. Tetrahedron: Asymmetry 2014, 25, 1376.

    Article  CAS  Google Scholar 

  68. Kim, S.; Kang, K.-T.; Kim, S.-G. Tetrahedron 2014, 70, 5114.

    Article  CAS  Google Scholar 

  69. Joshi, H.; Singh, V. K. Asian J. Org. Chem. 2022, 11, e202100053.

    CAS  Google Scholar 

  70. Maity R.; Chandra Pan, S. Org. Biomol. Chem. 2015, 13, 6825.

    Article  CAS  PubMed  Google Scholar 

  71. Leth, L. A.; Glaus, F.; Meazza, M.; Fu, L.; Thøgersen, M. K.; Bitsch, E. A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2016, 55, 15272.

    Article  CAS  Google Scholar 

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Correspondence to Nadezhda V. Vchislo.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(8/9), 384–393

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Vchislo, N.V., Verochkina, E.A. Syntheses of quinolines and their derivatives from α,β-unsaturated aldehydes. Chem Heterocycl Comp 58, 384–393 (2022). https://doi.org/10.1007/s10593-022-03102-w

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