Skip to main content
SpringerLink
Log in

The versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties Part 2*. Catalysis of Michael and Biginelli reactions and nucleophilic addition at C=X and C≡X bonds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The second part of review is devoted to the catalytic role of DABCO in Michael and Biginelli reactions, as well as nucleophilic addition at C=X and C≡X bonds.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) Bugaenko, D. I.; Karchava, A. V.; Yurovskaya, М. А. Chem. Heterocycl. Compd.2020, 56, 128. [Khim. Geterotsikl. Soedin.2020, 56, 128.] (b) Bugaenko, D. I. Chem. Heterocycl. Compd.2017, 53, 1277. [Khim. Geterotsikl. Soedin.2017, 53, 1277.] (c) Bugaenko, D. I.; Yurovskaya, M. A.; Karchava, A. V. J. Org. Chem. 2017, 82, 2136. b Bugaenko, D. I.; Karchava, A. V.; Yurovskaya, M. A. Russ. Chem. Rev. 2018, 87, 272. [Usp. Khim.2018, 87, 272.] (e) Bugaenko, D. I.; Yurovskaya, M. A.; Karchava, A. V. Org. Lett.2018, 20, 6389. c Bugaenko, D. I. Chem. Heterocycl. Compd. 2018, 54, 829. [Khim. Geterotsikl. Soedin.2018, 54, 829.]

  2. Dawange, M.; Parekh, N.; Kumbhar, A.; Dehaen, W.; Kusurkar, R. New J. Chem.2017, 41, 3612.

  3. Biswas, S.; Majee, D.; Dagar, A.; Samanta, S. Synlett2014, 2115.

  4. Biswas, S.; Majee, D.; Guin, S.; Samanta, S. J. Org. Chem.2017, 82, 10928.

  5. Majee, D.; Guin, S.; Biswas, S.; Samanta, S. ChemistrySelect2017, 2, 3423.

  6. Gao, Z.; Zhang, L.; Sun, Z.; Yu, H.; Xiao, Y.; Guo, H. Org. Biomol. Chem.2014, 12, 5691.

  7. Babu, G. N.; Ayalew, H. M.; Jain, S. Med. Chem. Res.2014, 23, 2608.

  8. Moustafa, M. S.; Al-Mousawi, S. M.; Selim, M. A.; Mosallam, A. M.; Elnagdi, M. H. Beilstein J. Org. Chem.2014, 10, 141.

  9. Ghozlan, S. A. S.; Ahmed, A. G.; Abdelhamid, I. A. J. Heterocycl. Chem. 2016, 53, 817.

  10. Dagar, A.; Biswas, S.; Mobin, S. M.; Samanta, S. Tetrahedron Lett.2016, 57, 3326.

  11. Gupta, N.; Bhojani, G.; Tak, R.; Jakhar, A.; Khan, N. H.; Chatterjee, S.; Kureshy, R. I. ChemistrySelect2017, 2, 10902.

  12. Liang, L.; Li, E.; Dong, X.; Huang, Y. Org. Lett. 2015, 17, 4914.

  13. Mohebata, R.; Yazdani-Elah-Abadi, A.; Simin, N. Polycyclic Aromat. Compd.2018, 38, 180.

  14. Meng, X.-S.; Jiang, S.; Xu, X.-Y.; Wu, Q.-X.; Gub, Y.-C.; Shi, D.-Q. RSC Adv. 2016, 6, 66630.

  15. Liu, Y.; Du, Y.; Yu, A.; Qin, D.; Meng, X. Tetrahedron2015, 71, 7706.

  16. Li, Y.; Liu, T.; Fu, W. Int. J. Quantum Chem. 2017, 117, 25408.

  17. Rainoldi, G.; Faltracco, M.; Lo Presti, L.; Silvani, A.; Lesma, G. Chem. Commun.2016, 11575.

  18. Xu, S.; Chen, J.; Shang, J.; Qing, Z.; Zhang, J.; Tang, Y. Tetrahedron Lett.2015, 56, 6456.

  19. Li, Y.; Du, S.; Dub, Z.; Chen, C. RSC Adv. 2016, 6, 82260.

  20. Keyume, A.; Esmayil, Z.; Wang, L.; Jun, F. Tetrahedron2014, 70, 3976.

  21. Rana, N. K.; Shukla, K.; Mahto, P.; Jha, R. K.; Singh, V. K. Tetrahedron2018, 74, 5270.

  22. Mohebata, R.; Yazdani-Elah-Abadi, A.; Maghsoodlou, M.-T.; Hazeri, N. Chin. Chem. Lett. 2017, 28, 943.

  23. Sanaeishoar, H.; Nazarpour, R.; Mohave, F. RSC Adv.2015, 5, 68571.

  24. Bangade, V. M.; Reddy, B. C.; Thakur, P. B.; Babu, B. M.; Meshram, H. M. Tetrahedron Lett.2013, 54, 4767.

  25. Becerra, D.; Raimondi, W.; Dauzonne, D.; Constantieux, T.; Bonne, D.; Rodriguez, J. Synthesis2017, 195.

  26. Bhagat, U. K.; Peddinti, R. K. Synlett2018, 99.

  27. Gurubrahamam, R.; Nagaraju, K.; Chen, K. Chem. Commun.2018, 6048.

  28. Saeedi, M.; Goli, F.; Mahdavi, M.; Asadipour, A.; Shafiee, A.; Foroumadi, A. J. Heterocycl. Chem. 2015, 52, 1150.

  29. Gomha, S. M.; Badrey, M. G.; Arafa, W. A. A. Heterocycles2016, 92, 1450.

  30. Asgharzadeh, R.; Imanzadeh, G.; Soltanzadeh, Z. Green Chem. Lett. Rev. 2017, 10, 80.

  31. Soltanzadeh, Z.; Imanzadeh, G.; Noroozi-Pesyan, N.; Şahin, E.; Hooshmand, H. Tetrahedron2016, 72, 1736.

  32. Bhagat, U. K.; Kamaluddin; Peddinti, R. K. Tetrahedron Lett.2017, 58, 298.

  33. Mola, L.; Font, J.; Bosch, L.; Caner, J.; Costa, A. M.; Etxebarría-Jardí, G.; Pineda, O.; de Vicente, D.; Vilarrasa, J. J. Org. Chem. 2013, 78, 5832.

  34. Jia, Q.; Chen, L.; Yang, G.; Wang, J.; Wei, J.; Du, Z. Tetrahedron Lett.2015, 56, 7150.

  35. Derabli, C.; Mahdjoub, S.; Boulcina, R.; Boumoud, B.; Merazig, H.; Debache, A. Chem. Heterocycl. Compd.2016, 52, 99. [Khim. Geterotsikl. Soedin.2016, 52, 99.]

  36. Tejedor, D.; Álvarez-Méndez, S. J.; López-Soria, J. M.; Martín, V. S.; García-Tellado, F. Eur. J. Org. Chem.2014, 198.

  37. Feng, W.; Wu, H.; Qian, H.; Li, Z.; Sun, X.; Wang, Z. J. Chem. Res. 2016, 40, 364.

  38. (a) Ghosh, M.; Hajra, A. Eur. J. Org. Chem.2015, 7836. (b) Bugaenko, D. I.; Karchava, A. V.; Yunusova, Z. A.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2019, 55, 483. [Khim. Geterotsikl. Soedin.2019, 55, 483.]

  39. Chong, Q.; Xin, X.; Wang, C.; Wu, F.; Wang, H.; Shi, J.-c.; Wan, B. J. Org. Chem.2014, 79, 2105.

  40. Liu, Y.; Zhang, Q.; Du, Y.; Yu, A.; Zhangb, K.; Meng, X. RSC Adv.2014, 4, 52629.

  41. Gurubrahamam, R.; Gao, B.-F.; Chen, Y. m.; Chan, Y.-T.; Tsai, M.-K.; Chen, K. Org. Lett. 2016, 18, 3098.

  42. Qian, S.; Li, M.; Liu, J.; Wang, C. J. Chem. Res. 2017, 41, 487.

  43. Singh, S. N.; Bopanni, R.; Jayaprakash, S.; Venkateshwara Reddy, K.; Ashfaq, M. A.; Shiva Kumar, K.; Pal, M. RSC Adv. 2014, 4, 24870.

  44. Ngo, T.-T.-D.; Kishi, K.; Sako, M.; Shigenobu, M.; Bournaud, C.; Toffano, M.; Guillot, R.; Baltaze, J.-P.; Takizawa, S.; Sasai, H.; Giang, V.-T. ChemistrySelect2016, 1, 5414.

  45. Xi, Q.-Z.; Gan, Z.-J.; Li, E.-Q.; Duan, Z. Eur. J. Org. Chem.2018, 4917.

  46. Biswas, S.; Dagar, A.; Mobin, S. M.; Samanta, S. Org. Biomol. Chem.2016, 14, 1940.

  47. García-García, C.; Redondo, M. C.; Ribagorda, M.; Carreño, M. C. Eur. J. Org. Chem.2014, 7377.

  48. Misra, A.; Sharma, S.; Sharma, D.; Dubey, S.; Mishra, A.; Kishore, D.; Dwivedi, J. J. Chem. Sci.2018, 130, 31.

  49. Zhang, Y.; Wang, Y.-P.; Ge, J.; Lai, G.-W.; Lu, D.-L.; Liu, J.-X.; Li, X. Tetrahedron Lett.2018, 59, 941.

  50. Bharathiraja, G.; Sathishkannan, G.; Punniyamurthy, T. J. Org. Chem. 2016, 81, 2670.

  51. Zhong, Y.; Ma, S.; Li, B.; Jiang, X.; Wang, R. J. Org. Chem.2015, 80, 6870.

  52. Zheng, L.; Qiao, Y.; Lua, M.; Chang, J. Org. Biomol. Chem.2015, 13, 7558.

  53. Luque-Agudo, V.; Albarrán-Velo, J.; Fernández-Bolaños, J. G.; López, O.; Light, M. E.; Padrón, J. M.; Lagunes, I.; Román, E.; Serrano, J. A.; Gil, M. V. New J. Chem.2017, 41, 3154.

  54. Cai, G.; Liu, S.; Zhang, J.; Ren, Y.; Wang, H.; Miao, Z. Synth. Commun. 2016, 46, 793.

  55. Liu, Y.; Ge, W.; Han, J.; Zhu, Y.; Shi, Y.; Wu, H. Tetrahedron Lett.2017, 58, 2665.

  56. (a) Bugaenko, D. I.; Karchava, A. V.; Yurovskaya, M. A. Russ. Chem. Rev. 2019, 88, 99. [Usp. Khim.2019, 88, 99.] (b) Singh, S.; Samanta, S. Chin. J. Chem.2015, 33, 1244.

  57. Ni, C.; Zhang, Y.; Hou, Y.; Tong, X. Chem. Commun.2017, 2567.

  58. Lone, A. M.; Bhat, B. A. Org. Biomol. Chem.2014, 12, 242.

  59. Biginelli, P. Ber. Dtsch. Chem. Ges.1891, 24(1), 1317.

  60. Foroughifar, N.; Beromi, S. K.; Pasdar, H.; Shahi, M. Iran. J. Pharm. Res.2017, 16, 596.

  61. Rimaz, M.; Khalafy, J.; Mousavi, H.; Bohlooli, S.; Khalili, B. J. Heterocycl. Chem. 2017, 54, 3174.

  62. Rimaz, M.; Khalafy, J.; Mousavi, H. Res. Chem. Intermed. 2016, 42, 8185.

Download references

Acknowledgement

This review article was prepared with financial support from the Russian Foundation for Basic Research (grant 18-33-01100).

Author information

Authors and Affiliations

  1. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119992, Russia

    Dmitry I. Bugaenko, Alexander V. Karchava & Marina A. Yurovskaya

Authors
  1. Dmitry I. Bugaenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alexander V. Karchava
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marina A. Yurovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marina A. Yurovskaya.

Additional information

* For Communication 1, see1а.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(2), 145–160

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bugaenko, D.I., Karchava, A.V. & Yurovskaya, M.A. The versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties Part 2*. Catalysis of Michael and Biginelli reactions and nucleophilic addition at C=X and C≡X bonds. Chem Heterocycl Comp 56, 145–160 (2020). https://doi.org/10.1007/s10593-020-02637-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02637-0

Keywords

Search

Navigation