Chinese Journal of Organic Chemistry >
Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction
Received date: 2022-09-21
Revised date: 2022-10-21
Online published: 2022-11-22
Supported by
National Natural Science Foundation of China(21871123)
A mild approach to prepare functionalized azetidines by intermolecular aza Paternò-Büchi reaction using suitable auxochrome (pyrazole) to promote 3-pyrazolyl quinoxalin-2(1H)-ones into its excited state has been developed. Overall, pyrazolyl plays a key role in reducing the excited state energy of the triplet state of quinoxalinones, changing the redox potential and subsequent transformation as a good leaving group. The cross-dehydrogenative coupling (CDC)-amination, aza Paternò-Büchi reaction, and elimination reaction were also investigated.
Chengjun Zhao , Zhiqin Bai , Jian He , Qiang Liu . Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4300 -4314 . DOI: 10.6023/cjoc202209028
| [1] | Richardson, A. D.; Becker, M. R.; Schindler, C. S. Chem. Sci. 2020, 11, 7553. |
| [2] | (a) Tsuge, O.; Tashiro, M.; Oe, K. Tetrahedron Lett. 1968, 9, 3971. |
| [2] | (b) Koch, T. H.; Howard, K. H. Tetrahedron Lett. 1972, 13, 4035. |
| [2] | (c) Koch, T. H.; Rodehorst, R. M. Tetrahedron Lett. 1972, 13, 4039. |
| [2] | (d) Howard, K. A.; Koch, T. H. J. Am. Chem. Soc. 1975, 97, 7288. |
| [2] | (e) Rodehorst, R. M.; Koch, T. H. J. Am. Chem. Soc. 1975, 97, 7298. |
| [2] | (f) Sa-kamoto, R.; Inada, T.; Sakurai, S.; Maruoka, K. Org. Lett. 2016, 18, 6252. |
| [3] | (a) Padwa, A. Chem. Rev. 1977, 77, 37. |
| [3] | (b) Pratt, A. C. Chem. Soc. Rev. 1977, 6, 63. |
| [3] | (c) Padwa, A.; Albrecht, F. J. Am. Chem. Soc. 1972, 94, 1000. |
| [3] | (d) Kandappa, S. K.; Valloli, L. K.; Ahuja, S.; Parthiban, J. Chem. Soc. Rev. 2021, 50, 1617. |
| [4] | Becker, M. R.; Wearing, E. R.; Schindler, C. S. Nat. Chem. 2020, 12, 898. |
| [5] | (a) Hyatt, J. A.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1972, 1144. |
| [5] | (b) Swenton, J. S.; Hyatt, J. A. J. Am. Chem. Soc. 1974, 96, 4879. |
| [5] | (c) Swenton, J. S.; Balchunis, R. J. J. Heterocycl. Chem 1974, 11, 917. |
| [5] | (d) Kumagai, T.; Kawamura, Y.; Mukai, T. Chem. Lett. 1983, 12, 1357. |
| [5] | (e) Kawamura, Y.; Kumagai, T.; Murai, T. Chem. Lett. 1985, 14, 1937. |
| [5] | (f) Becker, M. R.; Wearing, E. R.; Schindler, C. S. Nat. Chem. 2020, 12, 898. |
| [5] | (g) Futamura, S.; Ohta, H.; Kamiya, Y. Chem. Lett. 1980, 9, 655. |
| [5] | (h) Nishio, T. J. Org. Chem. 1984, 49, 827. |
| [5] | (i) Nishio, T.; Omote, Y. J. Org. Chem. 1985, 50, 1370. |
| [5] | (j) Nishio, T.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2611. |
| [5] | (k) Nishio, T. J. Chem. Soc., Perkin Trans. 1 1990, 565. |
| [5] | (l) Katagiri, N.; Kasai, K.; Kaneko, C. Chem. Pharm. Bull. 1986, 34, 4429. |
| [5] | (m) Li, X.; Gro?kopf, J.; Jandl, C.; Bach, T. Angew. Chem., Int. Ed. 2021, 60, 2684. |
| [6] | Kumarasamy, E.; Kandappa, S. K.; Raghunathan, R.; Jockusch, S.; Sivaguru, J. Angew. Chem., Int. Ed. 2017, 56, 7056. |
| [7] | Becker, M. R.; Richardson, A. D.; Schindler, C. S. Nat. Commun. 2019, 10, 5095. |
| [8] | Zhu, M.; Zhang, X.; Zheng, C.; You, S.-L. ACS Catal. 2020, 10, 12618. |
| [9] | (a) Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125. |
| [9] | (b) Li, K.-J.; Xu, K.; Liu, Y.-G.; Zeng, C.-C.; Sun, B.-G. Adv. Synth. Catal. 2019, 361, 1033. |
| [10] | Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873. |
| [11] | Sun, M.; Wang, L.; Zhao, L.; Wang, Z.; Li, P. ChemCatChem 2020, 12, 5261. |
| [12] | Niu, K.; Ding, L.; Zhou, P.; Hao, Y.; Liu, Y.; Song, H.; Wang, Q. Green Chem. 2021, 23, 3246. |
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