苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应研究

doi:10.6023/cjoc202108016

摘要/Abstract

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

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.

Key words: tin powder, allyl bromides, benzol[e][1,2,3]oxathiazine-2,2-dioxides, allylation

引用此文

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.

Feng Wang, Danfeng Huang, Pengfei Zhao, Ming Yang, Tongyu Han, Kehu Wang, Junjiao Wang, Yingpeng Su, Yulai Hu. Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 507-518.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

图1. 苯并[e][1,2,3] 噁噻嗪-2,2-二氧化物的烯丙基化反应

Scheme 1. Allylation reaction of benzol[e][1,2,3]oxathiazine 2,2-dioxides

Entry	Molar ratio of 1a/2/3a	Solvent	Yield^b/%
1	1/2/1.5	THF	88
2	1/2/2	THF	91
3^c	1/2/2.5	THF	98
4	1/2/3	THF	96
5	1/1.5/2.5	THF	92
6	1/2.5/2.5	THF	93
7	1/2/2.5	CH₃CH₂OH	57
8	1/2/2.5	1,4-Dioxane	91
9	1/2/2.5	H₂O	27
10	1/2/2.5	DCE	65
11	1/2/2.5	CH₃CN	62
12	1/2/2.5	Toluene	74
13	1/2/2.5	DCM	0

表1. 锡粉促进的烯丙基化反应的条件优化a

Table 1. Optimization of reaction conditions of tin powder- promoted allylation

表2. 锡粉促进下苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应a

Table 2. Allylation reaction of benzol[e][1,2,3] oxathiazine-2,2-dioxides promoted by tin powder

表3. 碱存在下产物4的烯丙基化反应a

Table 3. Allylation reaction of products 4 in the presence of base

表4. 碱存在下产物4的烯丙基化反应a

Table 4. Allylation reaction of products 4 in the presence of base

图2. 锡粉促进的烯丙基化反应的可能的反应机理

Scheme 2. Proposed reaction mechanism of allylation promoted by tin powder

参考文献 21

[1]	(a) Marshall, J. A. Chem. Rev. 1996, 96, 31. pmid: 11848743
	(b) Crich, D.; Grant, D.; Krishnamurthy, V.; Patel, M. Acc. Chem. Res. 2007, 40, 453. doi: 10.1021/ar600020v pmid: 11848743
	(c) Roy, U. K.; Roy. S. Chem. Rev. 2010, 110, 2472. doi: 10.1021/cr800336a pmid: 11848743
	(d) Kuang, Y.; Liu, X.; Chang, L.; Wang, M.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 3814. doi: 10.1021/ol201312y pmid: 11848743
[2]	(a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. doi: 10.1002/(ISSN)1521-3773
	(b) Mitchell, T. N. Synthesis 1992, 803.
	(c) Carsten, B.; He, F.; Son, H. J.; Xu, T.; Yu, L. Chem. Rev. 2011, 111, 1493. doi: 10.1021/cr100320w
	(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. doi: 10.1002/anie.201209262
[3]	Hoch, M. Appl. Geochem. 2001, 16, 719. doi: 10.1016/S0883-2927(00)00067-6
[4]	(a) Enholm, E. J.; Schulte II, J. P. Org. Lett. 1999, 1, 1275. doi: 10.1021/ol990945p
	(b) Cormier, M.; Ahmad, M.; Maddaluno, J.; Paolis, M. D. Organometallics 2017, 36, 4920. doi: 10.1021/acs.organomet.7b00765
	(c) Mahajani, N. S.; Chisholm, J. D. Org. Biomol. Chem. 2018, 16, 4008. doi: 10.1039/C8OB00687C
[5]	Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 10, 1527. doi: 10.1246/cl.1981.1527
[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.
	(b) Wang, X.; Huang, D.; Wang, K.-H.; Su, Y.; Hu, Y. J. Org. Chem. 2019, 84, 6946. doi: 10.1021/acs.joc.9b00733
	(c) Wang, S.; Wang, K.-H.; Chang, B.; Huang, D.; Hu, Y. Appl. Organomet. Chem. 2021, 35, e6249.
	(d) Deng, Z.; Yang, T.; Wang, K.-H.; Xue, W.; Huang, D.; Li, P.; Wang, J.; Su, Y.; Hu, Y. Tetrahedron 2020, 76, 131185. doi: 10.1016/j.tet.2020.131185
	(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) doi: 10.6023/cjoc202003002
	( 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.) doi: 10.6023/cjoc202003002
[8]	(a) Wang, K.-H.; Wang, J.; Wang, Y.; Su, Y.; Huang, D.; Fu, Y.; Du, Z.; Hu, Y. Synthesis 2018, 50, 1907. doi: 10.1055/s-0036-1591909
	(b) Yang, Z.; Huang, D.; Wen, L.; Wang, J.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1725. (in Chinese) doi: 10.6023/cjoc201801021
	( 杨政, 黄丹凤, 文岚, 王娟娟, 王克虎, 胡雨来, 有机化学, 2018, 38, 1725.) doi: 10.6023/cjoc201801021
[9]	(a) Kyowa, Y. H. K. K. US 6376687, 2002. pmid: 23136854
	(b) Peters, R. H.; Chao, W.-R.; Sato, B.; Shigeno, K.; Zaveri, N. T.; Tanabe, M. Steroids 2003, 68, 97. doi: 10.1016/S0039-128X(02)00118-6 pmid: 23136854
	(c) Woo, L. W. L; Purohi, A.; Potter, B. V. L. Mol. Cell. Endocrinol. 2011, 340, 175. doi: 10.1016/j.mce.2010.12.035 pmid: 23136854
	(d) Williams, S. J. Expert Opin. Ther. Pat. 2013, 23, 79. doi: 10.1517/13543776.2013.736965 pmid: 23136854
[10]	(a) Luo, Y.; Carnell, A. J.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 6762. doi: 10.1002/anie.201202136
	(b) Hepburn, H. B.; Chotsaeng, N.; Luo, Y.; Lam, H. W. Synthesis 2013, 45, 2649. doi: 10.1055/s-00000084
[11]	(a) Luo, Y.; Hepburn, H. B.; Chotsaeng, N.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 8309. doi: 10.1002/anie.v51.33
	(b) Hepburn, H. B.; Lam, H. W. Angew. Chem., Int. Ed. 2014, 53, 11605. doi: 10.1002/anie.201407233
	(c) Park, J.; Choi, S.; Lee, Y.; Cho, S. H. Org. Lett. 2017, 19, 4054. doi: 10.1021/acs.orglett.7b01821
	(d) Liu, J.; Tong, X.; Chen, M. J. Org. Chem. 2020, 85, 5193. doi: 10.1021/acs.joc.9b03222
	(e) Callingham, M.; Partridge, B. M.; Lewis, W.; Lam, H. W. Angew. Chem., Int. Ed. 2017, 56, 16352. doi: 10.1002/anie.v56.51
[12]	Gao, Z.; Zhang, L.; Sun, Z.; Yu, H.; Xiao, Y.; Guo, H. Org. Biomol. Chem. 2014, 12, 5691. doi: 10.1039/C4OB00840E
[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. doi: 10.1039/C5OB02260F
	(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) doi: 10.6023/cjoc201606013
	( 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.) doi: 10.6023/cjoc201606013
[14]	(a) Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. doi: 10.1016/S0040-4020(99)00227-6
	(b) Zhang, J.; Blazecka, P. G.; Berven, H.; Belmont, D. Tetrahedron Lett. 2003, 44, 5579. doi: 10.1016/S0040-4039(03)01380-7
	(c) Estevam, I. H. S.; Bieber, L. W. Tetrahedron Lett. 2003, 44, 667. doi: 10.1016/S0040-4039(02)02667-9
	(d) Lin, M.-H.; Hung, S.-F.; Lin, L.-Z.; Tsai, W.-S.; Chuang, T.-H. Org. Lett. 2011, 13, 332. doi: 10.1021/ol102825t
	(e) Lin, M.-H.; Lin, W.-C.; Liu, H.-J.; Chuang, T.-H. J. Org. Chem. 2013, 78, 1278. doi: 10.1021/jo302572s
	(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) doi: 10.6023/cjoc201411014
	( 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.)
	(g) Li, J.; Yang, T.; Zhang, H.; Huang, D.; Wang, K.; Su, Y.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 925. (in Chinese) doi: 10.6023/cjoc201611009
	( 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.) doi: 10.6023/cjoc201611009
[15]	(a) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452. doi: 10.1021/jo9901337
	(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. doi: 10.1021/cr00022a010
	(b) Shen, Z.-L.; Wang, S.-Y.; Chok, Y.-K.; Xu, Y.-H.; Loh, T.-P. Chem. Rev. 2013, 113, 271. doi: 10.1021/cr300051y
[17]	Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958. doi: 10.1021/ja029276s
[18]	Wang, Z.; Zha, Z.; Zhou, C. Org. Lett. 2002, 4, 1683. doi: 10.1021/ol0257326
[19]	Zha, Z.; Xie, Z.; Zhou, C.; Chang, M.; Wang, Z. New J. Chem. 2003, 27, 1297. doi: 10.1039/b303187j
[20]	(a) Kamal, A.; Sattur, P. B. Synthesis 1981, 272.
	(b) Wang, Y.-G.; Yu, C.-B.; Wang, D.-W.; Wang, X.-B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071. doi: 10.1021/ol800591u
[21]	Tripathi, C. B.; Mukherjee, S. Angew. Chem., Int. Ed. 2013, 52, 8450. doi: 10.1002/anie.v52.32