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Recent advances in dearomatization of benzazoles, purines, and caffeine (microreview)

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Chemistry of Heterocyclic Compounds Aims and scope

Dearomatization reactions are well established in organic synthesis and other research fields usually leading to structurally diverse polycyclic molecules or complex heterocyclic frameworks. In this microreview, recent development of dearomative functionalization of benzazoles, purines, and caffeine via cycloaddition or addition reaction has been summarized. This will help researchers to find the potential scientific value of dearomatization reactions in drug discovery.

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References

  1. (a) MacLeod, B. L.; Pienkos, J. A.; Wilson, K. B.; Sabat, M.; Myers, W. H.; Harman, W. D. Organometallics 2016, 35, 370. (b) Rossi-Ashton, J. A.; Clarke, A. K.; Taylor, R. J. K.; Unsworth, W. P. Org. Lett. 2020, 22, 1175. (c) Bertuzzi, G.; Sinisi, A.; Caruana, L.; Mazzanti, A.; Fochi, M.; Bernardi, L. ACS Catal. 2016, 6, 6473.

  2. (a) Shimizu, E. A.; Cory, B.; Hoang, J.; Castro, G. G.; Jung, M. E.; Vosburg, D. A. J. Chem. Educ. 2019, 96, 998. (b) Xu, X. J.; Wei, H.; Feng, H. D. Chem. Heterocycl. Compd. 2020, 56, 464. [Khim. Geterotsikl. Soedin. 2020, 56, 464.] (c) Feng, H. D. Chem. Heterocycl. Compd. 2020, 56, 506. [Khim. Geterotsikl. Soedin. 2020, 56, 506.] (d) Zhang, J. Y.; Li, J.; Ward, J. S.; Truong, K.-N.; Rissanen, K.; Albrecht, M. J. Org. Chem. 2020, 85, 12160. c Xu, X. J.; Van der Eycken, E. V.; Feng, H. D. Chin. J. Chem. 2020, 38, 1780.

  3. (a) Xia, Z.-L.; Xu-Xu, Q.-F.; Zheng, C.; You, S.-L. Chem. Soc. Rev. 2020, 49, 286. (b) Sharma, U. K.; Ranjan, P.; Van der Eycken, E. V.; You, S.-L. Chem. Soc. Rev. 2020, 49, 8721. (c) Yu, Q.; Fu, Y.; Huang, J.; Qin, J.; Zuo, H.; Wu, Y.; Zhong, F. ACS Catal. 2019, 9, 7285. (d) Cerveri, A.; Bandini M. Chine. J. Chem. 2020, 38, 287. (e) Romano, C.; Jia, M.; Monari, M.; Manoni, E.; Bandini, M. Angew. Chem., Int. Ed. 2014, 53, 13854.

  4. Gentry, P. R.; Kokubo, M.; Bridges, T. M.; Kett, N. R.; Harp, J. M.; Cho, H. P.; Smith, E.; Chase, P.; Hodder, P. S.; Niswender, C. M.; Daniels, J. S.; Conn, P. J.; Wood, M. R.; Lindsley, C. W. J. Med. Chem. 2013, 56, 9351.

    Article  CAS  Google Scholar 

  5. Yang, Z.-P.; Zheng, C.; Huang, L.; Qian, C.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 1530.

    Article  CAS  Google Scholar 

  6. Sahoo, S. C.; Joshi, M.; Pan, S. C. J. Org. Chem. 2017, 82, 12763.

    Article  Google Scholar 

  7. Zhang, S.-S.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 8026.

    Article  CAS  Google Scholar 

  8. (a) Zheng, Z.-B.; Cheng, W.-F.; Wang, L. J.; Zhu, J.; Sun, X.-L.; Tang, Y. Chin. J. Chem. 2020, 38, 1629. (b) Hao, Y. J.; Gong, Y.; Cao, Z. Y.; Zhou, Y.; Zhou, J. Chin. Chem. Lett. 2020, 31, 681.

  9. Wang, D.-C.; Xie, M.-S.; Guo, H.-M.; Qu, G.-R.; Zhang, M.-C.; You, S.-L. Angew. Chem., Int. Ed. 2016, 55, 14111.

    Article  CAS  Google Scholar 

  10. Zhang, M.-C.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M.; You, S.-L. Chem 2019, 5, 156.

    Article  CAS  Google Scholar 

  11. Hao, E.-J.; Fu, D.-D.; Wang, D.-C.; Zhang, T.; Qu, G.-R.; Li, G.-X.; Lan, Y.; Guo, H.-M. Org. Chem. Front. 2019, 6, 863.

    Article  CAS  Google Scholar 

  12. Liang, X.-A.; Liu, D. D.; Sun, H.; Jiang, C. Y.; Chen, H.; Niu, L. B.; Mahato, K.; Abdelilah, T.; Zhang, H.; Lei, A. W. Adv. Synth. Catal. 2020, 362, 1138.

    Article  CAS  Google Scholar 

  13. (a) Nassiri, M.; Milani, F. J.; Hassankhani, A. J. Heterocycl. Chem. 2015, 52, 1162. (b) Milani, F. J.; Nassiri, M. J. Heterocycl. Chem. 2017, 54, 1840.

  14. Xiong, Q.; Li, G. L.; Dong, S. X.; Liu, X. H.; Feng, X. M. Org. Lett. 2019, 21, 8771.

    Article  CAS  Google Scholar 

  15. Zhou, K.; Bao, M.; Huang, J. J.; Kang, Z. H.; Xu, X. F.; Hu, W. H.; Qian, Y. Org. Biomol. Chem. 2020, 18, 409.

    Article  CAS  Google Scholar 

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Financial support by the National Natural Science Foundation of China (Nos. 81973453 and 22078192) and the Shanghai University of Engineering Science (No. cs1804003) is gratefully acknowledged.

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Correspondence to Liliang Huang.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 525–527

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Huang, L., Feng, H. Recent advances in dearomatization of benzazoles, purines, and caffeine (microreview). Chem Heterocycl Comp 57, 525–527 (2021). https://doi.org/10.1007/s10593-021-02936-0

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  • DOI: https://doi.org/10.1007/s10593-021-02936-0

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