Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2506-2518.DOI: 10.6023/cjoc202211009 Previous Articles Next Articles
ARTICLES
收稿日期:
2022-11-08
修回日期:
2023-01-25
发布日期:
2023-02-14
通讯作者:
金杰
基金资助:
Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin()
Received:
2022-11-08
Revised:
2023-01-25
Published:
2023-02-14
Contact:
Jie Jin
Supported by:
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Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin. Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2506-2518.
Entry | Catalyst | Solvent | t/h | T/℃ | Yieldb/% |
---|---|---|---|---|---|
1 | NH4Cl | DMF | 8 | 125 | 35 |
2 | NH4Cl | MeCN | 12 | 80 | 47 |
3 | ZnCl2 | DMF | 8 | 125 | 60 |
4 | ZnCl2 | Ethylene glycol | 12 | 120 | None |
5 | ZnCl2 | iso-Propanol | 24 | 50 | 39 |
6 | ZnCl2 | MeCN | 12 | 80 | 90 |
Entry | Catalyst | Solvent | t/h | T/℃ | Yieldb/% |
---|---|---|---|---|---|
1 | NH4Cl | DMF | 8 | 125 | 35 |
2 | NH4Cl | MeCN | 12 | 80 | 47 |
3 | ZnCl2 | DMF | 8 | 125 | 60 |
4 | ZnCl2 | Ethylene glycol | 12 | 120 | None |
5 | ZnCl2 | iso-Propanol | 24 | 50 | 39 |
6 | ZnCl2 | MeCN | 12 | 80 | 90 |
Compd. | R | Yieldb/% | Compd. | R | Yieldb/% |
---|---|---|---|---|---|
5a | H | 81 | 5j | 3-Cl | 89 |
5b | 2,6-Me2 | 86 | 5k | 3-F | 80 |
5c | 2,6-Cl2 | 82 | 5l | 3-OMe | 81 |
5d | 2,6-F2 | 85 | 5m | 4-Br | 87 |
5e | 2-Me | 80 | 5n | 4-CMe3 | 80 |
5f | 2-Cl | 83 | 5o | 4-CF3 | 85 |
5g | 3,4-F2 | 84 | 5p | 4-CH3 | 81 |
5h | 3-Br | 87 | 5q | 4-CN | 89 |
5i | 3-Me | 86 | 5r | 4-NO2 | 82 |
Compd. | R | Yieldb/% | Compd. | R | Yieldb/% |
---|---|---|---|---|---|
5a | H | 81 | 5j | 3-Cl | 89 |
5b | 2,6-Me2 | 86 | 5k | 3-F | 80 |
5c | 2,6-Cl2 | 82 | 5l | 3-OMe | 81 |
5d | 2,6-F2 | 85 | 5m | 4-Br | 87 |
5e | 2-Me | 80 | 5n | 4-CMe3 | 80 |
5f | 2-Cl | 83 | 5o | 4-CF3 | 85 |
5g | 3,4-F2 | 84 | 5p | 4-CH3 | 81 |
5h | 3-Br | 87 | 5q | 4-CN | 89 |
5i | 3-Me | 86 | 5r | 4-NO2 | 82 |
Compd. | R | Yield/% | Compd. | R | Yieldb/% | |
---|---|---|---|---|---|---|
6a | H | 83 | 6i | 4-CF3 | 86 | |
6b | 2-Me | 84 | 6j | 4-CH2Cl | 91 | |
6c | 2-Cl | 89 | 6k | 4-Me | 92 | |
6d | 2-NO2 | 80 | 6l | 4-OMe | 83 | |
6e | 3,4-Cl2 | 85 | 6m | 4-Cl | 93 | |
6f | 3-Me | 92 | 6n | 4-CN | 86 | |
6g | 3-Cl | 85 | 6o | 4-F | 87 | |
6h | 4-Br | 88 | 6p | 4-NO2 | 92 |
Compd. | R | Yield/% | Compd. | R | Yieldb/% | |
---|---|---|---|---|---|---|
6a | H | 83 | 6i | 4-CF3 | 86 | |
6b | 2-Me | 84 | 6j | 4-CH2Cl | 91 | |
6c | 2-Cl | 89 | 6k | 4-Me | 92 | |
6d | 2-NO2 | 80 | 6l | 4-OMe | 83 | |
6e | 3,4-Cl2 | 85 | 6m | 4-Cl | 93 | |
6f | 3-Me | 92 | 6n | 4-CN | 86 | |
6g | 3-Cl | 85 | 6o | 4-F | 87 | |
6h | 4-Br | 88 | 6p | 4-NO2 | 92 |
[1] |
(a) Wang, Y.; Fang, Y. F.; Huang, W. H.; Zhou, X.; Wang, M. H.; Zhong, B.; Peng, D. Z. J. Ethnopharmacol. 2005, 98, 37.
doi: 10.1016/j.jep.2004.12.022 pmid: 30106158 |
(b) Cheng, Y.; Zhang, J. B.; Hou, W. P.; Wang, D. H.; Li, F. R.; Zhang, Y. Q.; Yuan, F. H. Int. Immunopharmacol. 2009, 9, 894.
doi: 10.1016/j.intimp.2009.03.014 pmid: 30106158 |
|
(c) Zhou, Y.; Liu, H. Y.; Song, J.; Cao, L.; Tang, L. M.; Qi, C. J. Mol. Med. Rep. 2018, 18, 3691.
doi: 10.3892/mmr.2018.9378 pmid: 30106158 |
|
(d) Dong, B. Med. Sci. Monit. 2018, 24, 3631.
doi: 10.12659/MSM.907589 pmid: 30106158 |
|
[2] |
Chen, S. P.; Zhou, Y. Q.; Sun, J.; Cao, F.; Braun, C.; Luo, F.; Ye, D. W.; Tian, Y. K. Mol. Pain 2018, 14, 1.
|
[3] |
Wang, Y.; Ma, D. L.; Jie, Y.; Wu, Y. Y.; Pan, Z. Q. Immunotherapy 2012, 4, 581.
doi: 10.2217/imt.12.45 |
[4] |
(a) Liu, Z.; Zheng, J. F.; Yang, L.Q.; Yi, L.; Hu, B. Acta Physiol. Sin. 2007, 59, 285 (in Chinese).
pmid: 17579782 |
(刘珍, 郑济芳, 杨露青, 易岚, 胡弼, 生理学报, 2007, 59, 285.)
pmid: 17579782 |
|
(b) Zhu, W. L.; Zhang, Y. N.; Huang, Y. J.; Lu, L. Int. Rev. Neurobiol. 2017, 135, 279.
pmid: 17579782 |
|
[5] |
(a) Qian, L.; Xu, Z. L.; Zhang, W.; Wilson, B.; Hong, J. S.; Flood, P. M. J. Neuroinflammation 2007, 4, 1.
doi: 10.1186/1742-2094-4-1 |
(b) Yang, Y. Q.; Wang, H. D.; Li, L. W.; Li, X.; Wang, Q.; Ding, H.; Wang, X. L.; Ye, Z. N.; Wu, L. Y.; Zhang, M. L.; Pan, H. Front. Neurosci. 2016, 10, 580.
|
|
[6] |
(a) Jiang, S. L.; Gao, Y. B.; Hou, W.; Liu, R.; Qi, X.; Xu, X.; Li, J.; Bao, H. G.; Hua, B. J. Oncol. Lett. 2016, 12, 1380.
doi: 10.3892/ol.2016.4768 |
(b) Song, L. Q.; Liu, D.; Zhao, Y.; He, J. J.; Kang, H. F.; Dai, Z. J.; Wang, X. J.; Zhang, S. Q.; Zan, Y. Biochem. Biophys. Res. Commun. 2015, 464, 705.
doi: 10.1016/j.bbrc.2015.07.004 |
|
(c) Yang, H. B.; Yin, P. H.; Shi, Z.; Ma, Y. C.; Zhao, C. G.; Zheng, J. P.; Chen, T. Oncol. Lett. 2016, 11, 411.
doi: 10.3892/ol.2015.3838 |
|
[7] |
(a) Luo, D. M.S. Thesis, Changsha University of Science & Technology, Changsha, 2013 (in Chinese).
|
(罗丹, 硕士论文,长沙理工大学,长沙, 2013.)
|
|
(b) Yang, F.; Guan, Z. J.; Cai, X. Y.; Wu, Q. Y.; Meng, Q. G. Acad. J. Second Mil. Med. Univ. 2015, 36, 413 (in Chinese).
|
|
(杨帆, 管忠俊, 柴晓云, 吴秋业, 孟庆国, 第二军医大学学报, 2015, 36, 413.)
|
|
[8] |
Xie, G. Y.; Zhang, Q.; Huang, Y. Y.; Zheng, H.; Ding, S. J. South-Cent. Univ. Natl. (Nat. Sci. Ed.) 2020, 39, 221 (in Chinese).
|
(谢光勇, 张倩, 黄业迎, 郑浩, 丁爽, 中南民族大学学报, 2020, 39, 221.)
|
|
[9] |
Kazemnejadi, M.; Mahmoudi, B.; Sharafi, Z.; Nasseri, M. A.; Allahresani, A.; Esmaeilpour, M. Appl. Organomet. Chem. 2020, 34, 1.
|
[10] |
(a) Demko, Z. P.; Sharpless, K. B. J. Org. Chem. 2001, 66, 7945.
doi: 10.1021/jo010635w pmid: 11722189 |
(b) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. Soc. 2003, 125, 9983.
doi: 10.1021/ja030204q pmid: 11722189 |
|
(c) Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 2824.
doi: 10.1016/j.tetlet.2008.02.115 pmid: 11722189 |
|
(d) Das, B.; Reddy, C.; Kumar, D. Synlett 2010, 391.
pmid: 11722189 |
|
(e) Harusawa, S.; Yoneyama, H.; Usami, Y.; Komeda, S. Synthesis 2013, 45, 1051.
doi: 10.1055/s-00000084 pmid: 11722189 |
|
(f) Myznikov, L.; Vorona, S.; Artamonova, T.; Zevatskii, Y. Synthesis 2014, 46, 0781.
doi: 10.1055/s-00000084 pmid: 11722189 |
|
(g) Coca, A.; Turek, E.; Feinn, L. Synth. Commun. 2015, 45, 218.
doi: 10.1080/00397911.2014.957775 pmid: 11722189 |
|
(h) Coca, A.; Feinn, L.; Dudley, J. Synth. Commun. 2015, 45, 1023.
doi: 10.1080/00397911.2014.989451 pmid: 11722189 |
|
(i) Myznikov, L. V.; Vorona, S. V.; Artamonova, T. V. Russ. J. Gen. Chem. 2017, 87, 731.
doi: 10.1134/S1070363217040119 pmid: 11722189 |
|
(j) Witkowski, T. G.; Sebastiao, E.; Gabidullin, B.; Hu, A.; Zhang, F.; Murugesu, M. ACS Appl. Energy Mater. 2018, 1, 589.
doi: 10.1021/acsaem.7b00138 pmid: 11722189 |
|
[11] |
(a) Seldes, A. M.; Accorso, N. D.; Souto, M. F.; Alho, M. M.; Arabehety, C. G. J. Mass Spectrom. 2001, 36, 1069.
pmid: 33403303 |
(b) Reichart, B.; Kappe, C. O. Tetrahedron Lett. 2012, 53, 952.
doi: 10.1016/j.tetlet.2011.12.043 pmid: 33403303 |
|
(c) Jia, Y. H.; Yang, K. X.; Chen, S. L. J. Phys. Chem. A 2017, 122, 8.
doi: 10.1021/acs.jpca.7b08078 pmid: 33403303 |
|
(d) Obydennov, D. L.; SimbIR ATRtseva, A. E.; Piksin, S. E.; Sosnovskikh, V. Y. ACS Omega 2020, 5, 33406.
doi: 10.1021/acsomega.0c05357 pmid: 33403303 |
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