苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应研究
收稿日期: 2021-08-13
修回日期: 2021-09-30
网络出版日期: 2022-02-24
基金资助
国家自然科学基金(21861033); 国家自然科学基金(22061037); 上海恩氟佳科技有限公司资助项目.
Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides
Received date: 2021-08-13
Revised date: 2021-09-30
Online published: 2022-02-24
Supported by
National Natural Science Foundation of China(21861033); National Natural Science Foundation of China(22061037); Shanghai Sinofluoro Chemicals Co., Ltd.
探索了锡粉促进下苯并[e][1,2,3]噁噻嗪-2,2-二氧化物与烯丙基溴的烯丙基化反应. 研究结果表明: 各种底物都能顺利发生烯丙基化反应并且产物产率高; 当用烯丙基溴衍生物进行反应时, 得到的都是γ-加成产物. 该烯丙基化反应产物在碱的促进下可发生N-烯丙基化反应, 得到苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的双烯丙基化产物. 该双烯丙基化产物进一步发生关环复分解反应, 得到苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的环状衍生物.
关键词： 锡粉; 烯丙基溴; 苯并[e][1,2,3]噁噻嗪-2,2-二氧化物; 烯丙基化反应
王凤 , 黄丹凤 , 赵鹏飞 , 杨明 , 韩侗育 , 王克虎 , 王君姣 , 苏瀛鹏 , 胡雨来 . 苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应研究[J]. 有机化学, 2022 , 42(2) : 507 -518 . DOI: 10.6023/cjoc202108016
The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was explored. The results showed that the allylation proceeded smoothly with high yields for a variety of substrates. When various allyl bromides were used to perform the reaction, the γ-addition products were obtained. These allylated products underwent N-allylation reaction in the presence of base, and the diallylated products of benzol[e][1,2,3]oxathiazine-2,2-dioxides were obtained in high yields. The diallylated products of benzol[e][1,2,3] oxathiazine-2,2-dioxides further underwent ring closing metathesis reaction, and the cyclic derivatives of benzol[e][1,2,3] oxathiazine-2,2-dioxides were obtained in good yield.
| [1] | (a) Marshall, J. A. Chem. Rev. 1996, 96, 31. |
| [1] | (b) Crich, D.; Grant, D.; Krishnamurthy, V.; Patel, M. Acc. Chem. Res. 2007, 40, 453. |
| [1] | (c) Roy, U. K.; Roy. S. Chem. Rev. 2010, 110, 2472. |
| [1] | (d) Kuang, Y.; Liu, X.; Chang, L.; Wang, M.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 3814. |
| [2] | (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. |
| [2] | (b) Mitchell, T. N. Synthesis 1992, 803. |
| [2] | (c) Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. Chem. Rev. 2011, 111, 1493. |
| [2] | (d) delPozo, J.; Carrasco, D.; Pérez-Temprano, M. H.; García- Melchor, M.; Álvarez, R.; Casares, J. A.; Espinet P. Angew. Chem., Int. Ed. 2013, 52, 2189. |
| [3] | Hoch, M. Appl. Geochem. 2001, 16, 719. |
| [4] | (a) Enholm, E. J.; Schulte II, J. P. Org. Lett. 1999, 1, 1275. |
| [4] | (b) Cormier, M.; Ahmad, M.; Maddaluno, J.; Paolis, M. D. Organometallics 2017, 36, 4920. |
| [4] | (c) Mahajani, N. S.; Chisholm, J. D. Org. Biomol. Chem. 2018, 16, 4008. |
| [5] | Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 10, 1527. |
| [6] | Elaas, N. A.; Elaas, W. A.; Huang, D.; Hu, Y.; Wang, K.-H. Curr. Org. Synth. 2017, 14, 1156. |
| [7] | (a) Wang, X.; Huang, D.; Wang, K.-H.; Liu, J.; Zong, W.; Wang, J.; Su, Y.; Hu, Y. Appl. Organomet. Chem. 2019, 33, e4995. |
| [7] | (b) Wang, X.; Huang, D.; Wang, K.-H.; Su, Y.; Hu, Y. J. Org. Chem. 2019, 84, 6946. |
| [7] | (c) Wang, S.; Wang, K.-H.; Chang, B.; Huang, D.; Hu, Y. Appl. Organomet. Chem. 2021, 35, e6249. |
| [7] | (d) Deng, Z.; Yang, T.; Wang, K.-H.; Xue, W.; Huang, D.; Li, P.; Wang, J.; Su, Y.; Hu, Y. Tetrahedron 2020, 76, 131185. |
| [7] | (e) Zhao, Z.; Wang, J.; Huang, D.; Yang, Z.; Zhao, F.; Hu, Y.; Xu, W.; Hu, Y. Chin. J. Org. Chem. 2020, 40, 2026. (in Chinese) |
| [7] | ( 赵转霞, 王君姣, 黄丹凤, 杨政, 赵芳霞, 虎永琴, 徐炜刚, 胡雨来, 有机化学, 2020, 40, 2026.) |
| [8] | (a) Wang, K.-H.; Wang, J.; Wang, Y.; Su, Y.; Huang, D.; Fu, Y.; Du, Z.; Hu, Y. Synthesis 2018, 50, 1907. |
| [8] | (b) Yang, Z.; Huang, D.; Wen, L.; Wang, J.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1725. (in Chinese) |
| [8] | ( 杨政, 黄丹凤, 文岚, 王娟娟, 王克虎, 胡雨来, 有机化学, 2018, 38, 1725.) |
| [9] | (a) Kyowa, Y. H. K. K. US 6376687, 2002. |
| [9] | (b) Peters, R. H.; Chao, W.-R.; Sato, B.; Shigeno, K.; Zaveri, N. T.; Tanabe, M. Steroids 2003, 68, 97. |
| [9] | (c) Woo, L. W. L; Purohi, A.; Potter, B. V. L. Mol. Cell. Endocrinol. 2011, 340, 175. |
| [9] | (d) Williams, S. J. Expert Opin. Ther. Pat. 2013, 23, 79. |
| [10] | (a) Luo, Y.; Carnell, A. J.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 6762. |
| [10] | (b) Hepburn, H. B.; Chotsaeng, N.; Luo, Y.; Lam, H. W. Synthesis 2013, 45, 2649. |
| [11] | (a) Luo, Y.; Hepburn, H. B.; Chotsaeng, N.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 8309. |
| [11] | (b) Hepburn, H. B.; Lam, H. W. Angew. Chem., Int. Ed. 2014, 53, 11605. |
| [11] | (c) Park, J.; Choi, S.; Lee, Y.; Cho, S. H. Org. Lett. 2017, 19, 4054. |
| [11] | (d) Liu, J.; Tong, X.; Chen, M. J. Org. Chem. 2020, 85, 5193. |
| [11] | (e) Callingham, M.; Partridge, B. M.; Lewis, W.; Lam, H. W. Angew. Chem., Int. Ed. 2017, 56, 16352. |
| [12] | Gao, Z.; Zhang, L.; Sun, Z.; Yu, H.; Xiao, Y.; Guo, H. Org. Biomol. Chem. 2014, 12, 5691. |
| [13] | (a) Du, G.; Huang, D.; Wang, K.-H; Chen, X.; Xu, Y.; Ma, J.; Su, Y.; Fu, Y.; Hu, Y. Org. Biomol. Chem. 2016, 14, 1492. |
| [13] | (b) Chang, Q.; Kang, J.; Zhang, W.; Wang, J.; Huang, D.; Wang, K.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2016, 36, 2920. (in Chinese) |
| [13] | ( 常青, 康娟, 张为钢, 王娟娟, 黄丹凤, 王克虎, 苏瀛鹏, 胡雨来, 有机化学, 2016, 36, 2920.) |
| [14] | (a) Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. |
| [14] | (b) Zhang, J.; Blazecka, P. G.; Berven, H.; Belmont, D. Tetrahedron Lett. 2003, 44, 5579. |
| [14] | (c) Estevam, I. H. S.; Bieber, L. W. Tetrahedron Lett. 2003, 44, 667. |
| [14] | (d) Lin, M.-H.; Hung, S.-F.; Lin, L.-Z.; Tsai, W.-S.; Chuang, T.-H. Org. Lett. 2011, 13, 332. |
| [14] | (e) Lin, M.-H.; Lin, W.-C.; Liu, H.-J.; Chuang, T.-H. J. Org. Chem. 2013, 78, 1278. |
| [14] | (f) Wang, F.; Lu, A.; Huang, D.; Su, Y.; Xia, X.; Xü, Y.; Wang, K.-H.; Hu, Y. Chin. J. Org. Chem. 2015, 35, 1046. (in Chinese) |
| [14] | ( 王凤娇, 陆爱玲, 黄丹凤, 苏瀛鹏, 夏晓文, 徐艳丽, 王克虎, 胡雨来, 有机化学, 2015, 35, 1046.) |
| [14] | (g) Li, J.; Yang, T.; Zhang, H.; Huang, D.; Wang, K.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 925. (in Chinese) |
| [14] | ( 李军, 杨天宇, 张怀远, 黄丹凤, 王克虎, 苏瀛鹏, 胡雨来, 有机化学, 2017, 37, 925.) |
| [15] | (a) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452. |
| [15] | (b) Zha, Z.; Qiao, S.; Jiang, J.; Wang, Y.; Miao, Q.; Wang, Z. Tetrahedron 2005, 61 2521. |
| [16] | (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93. 2207. |
| [16] | (b) Shen, Z.-L.; Wang, S.-Y.; Chok, Y.-K.; Xu, Y.-H.; Loh, T.-P. Chem. Rev. 2013, 113, 271. |
| [17] | Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958. |
| [18] | Wang, Z.; Zha, Z.; Zhou, C. Org. Lett. 2002, 4, 1683. |
| [19] | Zha, Z.; Xie, Z.; Zhou, C.; Chang, M.; Wang, Z. New J. Chem. 2003, 27, 1297. |
| [20] | (a) Kamal, A.; Sattur, P. B. Synthesis 1981, 272. |
| [20] | (b) Wang, Y.-G.; Yu, C.-B.; Wang, D.-W.; Wang, X.-B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071. |
| [21] | Tripathi, C. B.; Mukherjee, S. Angew. Chem., Int. Ed. 2013, 52, 8450. |
/
| 〈 |
|
〉 |
