Chinese Journal of Organic Chemistry >
Aerobic Construction of 2-Acyl Benzoxazole by Tandem C—H Oxygenation and Oxazole Ring Formation
Received date: 2021-09-18
Revised date: 2021-10-14
Online published: 2021-10-21
Supported by
Natural Science Foundation of Jiangxi Province(20202BABL203008)
The synthesis of useful 2-acyl benzoxazoles has been realized via the tandem methylene C—H oxygenation and oxazole annulation of N-(o-hydroxyphenyl)phenylacetamides via copper catalysis in one-pot fashion. Besides featuring the incomparable step-economy resulting from the multi-step transformation, the tunable synthesis of diverse 2-methylene functionalized benzoxazoles using identical starting materials as well as the expanded synthesis of corresponding benzothiazoles is also attractive advantage of the work.
Key words： tandem; C—H oxygenation; annulation; 2-acyl benzoxazole; selectivity
Zhi Tu , Baoli Zhao , Jieping Wan , Chaoli Wang , Yunyun Liu . Aerobic Construction of 2-Acyl Benzoxazole by Tandem C—H Oxygenation and Oxazole Ring Formation[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4780 -4788 . DOI: 10.6023/cjoc202109029
| [1] | For selected reviews, see: (a) Ghoshal, T.; Patel, T. M. Future J. Pharm. Sci. 2020, 6, no. 94. |
| [1] | (b) Sattar, R.; Mukhtar, R.; Atif, M.; Hasnain, M.; Irfan, A. J. Heterocycl. Chem. 2020, 57, 2079. |
| [1] | (c) Singh, S.; Veeraswamy, G.; Bhattarai, D.; Goo, J.-I.; Lee, K.; Choi, Y. Asian J. Org. Chem. 2015, 4, 1338. |
| [1] | (c) Sun, Z.; Xu, M.; Wang, Y.; Hu, X. Chin. J. Org. Chem. 2020, 40, 4203. (in Chinese) |
| [1] | ( 孙泽众, 徐苗, 王云侠, 胡向东, 有机化学, 2020, 40, 4203.) |
| [2] | (a) Myllymäki, M. J.; Saario, S. M.; Kataja, A. O.; Castillo- Melendez, J. A.; Nevalainen, T.; Juvonen, R. O.; Jävinen, T.; Koshinen, A. M. P. J. Med. Chem. 2007, 50, 4236. |
| [2] | (b) Boger, D. L.; Sato, H.; Lerner, A. E.; Hedrick, M. P.; Fecik, R. A.; Miyauchi, H.; Wikie, G. D.; Austin, B. J.; Patricelli, M. P.; Cravatt, B. F. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 5044. |
| [3] | Janssen, F. J.; Baggelaar, M. P.; Hummel, J. J. A.; Overkleeft, H. S.; Cravatt, B. F.; Boger, D. L.; van der Stelt, M. J. Med. Chem. 2015, 58, 9742. |
| [4] | McGrath, M. E.; Sprengeler, P. A.; Hill, C. M.; Martichonok, V.; Cheung, H.; Somoza, J. R.; Palmer, J. T.; Janc, J. W. Biochemistry 2003, 42, 15018. |
| [5] | Tully, D. C.; Vidal, A.; Chatterjee, A. K.; Williams, J. A.; Roberts, M. J.; Petrassi, H. M.; Sraggon, G.; Bursulaya, B.; Pacoma, R.; Shipway, A.; Schumacher, A. M.; Danahay, H.; Harris, J. L. Bioorg. Med. Chem. Lett. 2008, 18, 5895. |
| [6] | Wolfart, K.; Molar, A.; Kawase, M.; Motohashi, N.; Molnar, J. Biol. Pharm. Bull. 2004, 27, 1462. |
| [7] | (a) Huang, J.; Zhou, Z.; Zhou, M.; Miao, M.; Li, H.; Hu, Q. Bioorg. Med. Chem. 2018, 26, 1653. |
| [7] | (b) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. |
| [7] | (c) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448. |
| [8] | For a recent review, see: Aljaar, N.; Gujjarappa, R.; Al-Refai, M.; Shtaiwi, M.; Malakar, C. C.. J. Heterocycl. Chem. 2019, 56, 2730. |
| [9] | Wu, X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., nt. Ed. 2010, 49, 7316. |
| [10] | (a) Karthik, S.; Gandhi, T. Org. Lett. 2017, 19, 5486. |
| [10] | (b) Yang, K.; Chen, X.; Wang, Y.; Li, W.; Kadi, A. A.; Fun, H.-K.; Sun, H.; Zhang, Y.; Li, G.; Lu, H. J. Org. Chem. 2015, 80, 11065. |
| [10] | (c) Yang, K.; Zhang, C.; Wang, P.; Zhang, Y.; Ge, H. Chem.-Eur. J. 2014, 20, 7241. |
| [10] | (d) Sharma, U. K.; Sharma, N.; Xu, J.; Song, G.; Van der Eycken, E. V. Chem.-Eur. J. 2015, 21, 4908. |
| [11] | (a) Boominathan, S. S. K.; Hu, W.-P.; Senadi, G. C.; Vandavsi, J. K.; Wang, J.-J. Chem. Commun. 2014, 50, 6726. |
| [11] | (b) Jiang, J.; Zou, H.; Dong, Q.; Wang, R.; Lu, L.; Zhu, Y.; He, W. J. Org. Chem. 2016, 81, 51. |
| [11] | (c) Alijaar, N.; Malakar, C. C.; Conrad, J.; Beifuss, U. J. Org. Chem. 2015, 80, 10829. |
| [11] | (d) Dhameliya, T. M.; Chourasiya, S. S.; Mishra, E.; Jadhavar, Bharatam, P. S. P. V.; Chakraborti, A. K. J. Org. Chem. 2017, 82, 10077. |
| [12] | (a) Wang, H.; Liu, J.; Qu, J.-P.; Kang, Y.-B. J. Org. Chem. 2020, 85, 3942. |
| [12] | (b) Bao, K.; Li, F.; Liu, H.; Wang, Z.; Shen, Q.; Wang, J.; Zhang, W. Sci. Rep. 2015, 5, no. 10360. |
| [12] | (c) Wu, Y.; Choy, P. Y.; Mao, F.; Kwong, F. Y. Chem. Commun. 2013, 49, 689. |
| [13] | (a) Cui, L.; He, Y.; Fan, X. Chin. J. Chem. 2012, 30, 992. |
| [13] | (b) Fan, X.; He, Y.; Zhang, X.; Guo, S.; Wang, Y. Tetrahedron 2011, 67, 6369. |
| [14] | (a) Pridgen, L. N.; Shilcrat, S. C. Synthesis 1984, 1048. |
| [14] | (b) Jutzi, P.; Gilge, U. J. Heterocycl. Chem. 1982, 20, 1011. |
| [14] | (c) Lester, R. P.; Bham, T.; Bousfield, T. W.; Lewis, W.; Camp, J. E. J. Org. Chem. 2016, 81, 12472. |
| [15] | (a) Liu, Y.; Zhang, Y.; Wan, J.-P. J. Org. Chem. 2017, 82, 8950. |
| [15] | (b) Tu, Z.; Du, Y.; Cao, X.; Liu, Y. Adv. Synth. Catal. 2019, 361, 4989. |
| [15] | (c) Chen, X.; Liu, Y. Tetrahedron 2018, 74, 3691. |
| [15] | (d) Tian, S.; Wang, C.; Xia, J.; Wan, J.-P.; Liu, Y. Adv. Synth. Catal. 2021, 363, 4627. |
| [15] | (e) Wang, L.; Liu, X.; Liu, J.-b.; Shen, J.; Chen, Q.; He, M.-Y. Chem. Asian J. 2018, 13, 765. |
| [16] | For selected recent reviews on C-H bond activation or functionalization, see: (a) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192. |
| [16] | (b) Xu, X.; Chen, D.; Wang, Z. Chin. J. Org. Chem. 2019, 39, 3338. (in Chinese) |
| [16] | ( 徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, 3338.) |
| [16] | (c) Tian, S.; Luo, T.; Zhu, Y.; Wan, J.-P. Chin. Chem. Lett. 2020, 31, 3073. |
| [16] | (d) Zhao, B.; Liu, Y. Synthesis 2020, 52, 3211. |
| [16] | (e) Yuan, X.; Yang, G.; Yu, B. Chin. J. Org. Chem. 2020, 40, 3620. (in Chinese) |
| [16] | ( 袁晓亚, 杨国平, 於兵, 有机化学, 2020, 40, 3620.) |
| [16] | (f) Luo, T.; Tian, S.; Wan, J.-P.; Liu, Y. Curr. Org. Chem. 2021, 25, 1180. |
| [17] | For some recent references on aerobic C-H transformation, see: (a) Boess, E.; Hoof, M. V.; Birdsall, S. L.; Klussmann, M. J. Org. Chem. 2020, 85, 1972. |
| [17] | (b) Gui, Q.-W.; Teng, F.; Li, Z.-C.; Jin, X.-F.; Zhang, M.; Dai, J.-N.; Lin, Y.-W.; Cao, Z.; He, W.-M. Org. Chem. Front. 2020, 7, 4026. |
| [17] | (c) Bao, P.; Liu, F.; Lv, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492. |
| [17] | (d) Xie, L.-Y.; Liu, Y.-S.; Ding, H.-R.; Gong, S.-F.; Tan, J.-X.; He, J.-Y.; Cao, Z.; He, W.-M. Chin. J. Catal. 2020, 41, 1168. |
| [17] | (e) Tanimoto, K.; Ohkado, R.; Lida, H. J. Org. Chem. 2019, 84, 14980. |
| [17] | (f) Abdukader, A.; Wang, R.; Mamat, M.; Liu, C. Chin. J. Org. Chem. 2020, 40, 1697. (in Chinese) |
| [17] | ( 阿布力米提•阿布都卡德尔, 汪荣, 买尔哈巴•买买提, 刘晨江, 有机化学, 2020, 40, 1697.) |
| [17] | (g) Sun, K.; Li, Y.; Feng, R.; Mu, S.; Wang, X.; Zhang, B. J. Org. Chem. 2020, 85, 1001. |
| [17] | (h) Wang, Y.; Liu, Y. Acta Chim. Sinica 2019, 77, 418. (in Chinese) |
| [17] | ( 王昱赟, 刘云云, 化学学报, 2019, 77, 418.) |
| [17] | (i) Yao, B.; Wu, J.; Wang, Y.; Jiang, H. Chin. J. Org. Chem. 2020, 40, 3044. (in Chinese) |
| [17] | ( 姚彪, 巫佳浩, 汪钰, 江焕峰, 有机化学, 2020, 40, 3044.) |
| [18] | Sun, A.; Prussia, A.; Zhan, W. Q.; Murray, E. E.; Doyle, J.; Cheng, L. T.; Yoon, J. J.; Radchenko, E. V.; Palyulin, V. A.; Compans, R. W.; Liotta, D. C.; Plemper, R. K.; Snyder, J. P. J. Med. Chem. 2006, 49, 5080. |
| [19] | (a) Pan, W.-J.; Wang, Z.-X. Asian J. Org. Chem. 2018, 7, 1626. |
| [19] | (b) Xie, P.; Huang, H. M.; Xie, Y. J.; Guo, S. M.; Xia, C. G. Adv. Synth. Catal. 2012, 354, 1692. |
| [20] | Ji, Y.-Y.; Zhang, Y.; Hu, Y.-Y.; Shao, L.-X. Tetrahedron 2015, 71, 6818. |
| [21] | Niu, Z.-J.; Li, L.-H.; Liu, X.-Y.; Liang, Y.-M. Adv. Synth. Catal. 2019, 361, 5217. |
| [22] | Nguyen, T. B.; Retailleau, P. Org. Lett. 2017, 19, 3887. |
/
| 〈 |
|
〉 |
