分子碘-炔酰胺-腈的三组分一锅反应:1,3,5-噁二嗪-2-酮衍生物的简便合成
收稿日期: 2015-05-30
修回日期: 2015-06-10
网络出版日期: 2015-06-19
基金资助
国家自然科学基金(Nos. U1204204, 21172139, 21202095)和河南省科技攻关(No. 142102210635)资助项目.
Facile Synthesis of 1,3,5-Oxadiazin-2-one Derivatives through Three-Component One-Pot Cyclization of Molecular Iodine, Ynamides and Nitriles
Received date: 2015-05-30
Revised date: 2015-06-10
Online published: 2015-06-19
Supported by
Project supported by the National Natural Science Foundation of China (Nos. U1204204, 21172139, 21202095) and the Science and Technology Key Project of Henan Province (No. 142102210635).
在便宜易得的分子碘促进及室温条件下, 通过炔酰胺与腈的分子间环化, 合成了一系列1,3,5-噁二嗪-2-酮衍生物. 该方法具有反应条件温和、操作简单、原料易得、反应迅速的特点. 通过1H NMR, 13C NMR, IR和HRMS对产物结构进行表征.
关键词： 炔酰胺; 碘; 1,3,5-噁二嗪-2-酮; 合成
孟团结 , 陈荣祥 , 刘澜涛 , 王涛 , 刘新明 , 赵文献 . 分子碘-炔酰胺-腈的三组分一锅反应:1,3,5-噁二嗪-2-酮衍生物的简便合成[J]. 有机化学, 2015 , 35(10) : 2108 -2113 . DOI: 10.6023/cjoc201505048
A series of 1,3,5-oxadiazin-2-one derivatives were obtained from the intermolecular cyclization of ynamides and nitriles mediated by cheap and readily available molecular iodine under room temperature. This protocol has some distinct advantages of mild conditions, simple work-up, easily available starting materials and fast reaction rate. The structures of all products were characterized by 1H NMR, 13C NMR, IR and HRMS.
Key words： ynamides; iodine; 1,3,5-oxadiazin-2-ones; synthesis
[1] (a) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028. (b) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937. (c) Luo, P.; Tang, R.; Zhong, P.; Li, J. Chin. J. Org. Chem. 2009, 29, 1924 (in Chinese).(罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.)
[2] (a) Cook, A. M.; Wolf, C. Tetrahedron Lett. 2015, 56, 2377.(b) Wang, X.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560.(c) Evano, G.; Gaumont, A.-C.; Alayrac, C.; Wrona, I. E.; Giguere, J. R.; Delacroix, O.; Bayle, A.; Jouvin, K.; Theunissen, C.; Gatignol, J.; Silvanus, A. C. Tetrahedron 2014, 70, 1529.(d) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064.(e) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840.(f) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 10, 1379.
[3] (a) Huang, H.; Zhu, X.; He, G.; Liu, Q.; Fan, J.; Zhu, H. Org. Lett. 2015, 17, 2510.(b) Lu, Z.; Cui, W.; Xia, S.; Bai, Y.; Luo, F.; Zhu, G. J. Org. Chem. 2012, 77, 9871.(c) Lu, Z.; Xu, X.; Yang, Z.; Kong, L.; Zhu, G. Tetrahedron Lett. 2012, 53, 3433.(d) Lu, Z.; Yang, Z.; Cui, W.; Zhu, G. Chem. Lett. 2012, 41, 636.(e) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.(f) Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763. (g) Huang, H.; He, G.; Zhu, G.; Zhu, X.; Qiu, S.; Zhu, H. J. Org. Chem. 2015, 80, 3480.
[4] Davies, P. W.; Cremonesi, A.; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931.
[5] Ferrini, S.; Chandanshive, J, Z.; Lena, S.; Franchini, M. C.; Giannini, G.; Tafi, A.; Taddei, M. J. Org. Chem. 2015, 80, 2562.
[6] (a) Okitsu, T.; Nakata, K.; Nishigaki, K.; Michioka, N.; Karatani, M.; Wada, A. J. Org. Chem. 2014, 79, 5914.(b) Kong, Y.; Jiang, K.; Cao, J; Fu, L.; Yu, L.; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Org. Lett. 2013, 15, 422.(c) Kong, Y.; Yu, L.; Fu, L.; Cao, J; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Synthesis 2013, 45, 1975.
[7] (a) Shen, C.-H.; Pan, Y.; Yu, Y.-F.; Wang, Z.-S; He, W.; Li, T.; Ye, L.-W. J Organomet. Chem. 2015, 795, 63. (b) Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2014, 16, 3138.(c) Gati, W.; Couty, F.; Boubaker, T.; Rammah, M. M.; Rammah, M. B.; Evano, G. Org. Lett. 2013, 15, 3122.(d) Dooleweerdt, K.; Ruhland, T.; Skrydstrup, T. Org. Lett. 2009, 11, 221.(e) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
[8] (a) Tokimizu, Y.; Wieteck, M.; Rudolph, M.; Oishi, S.; Fujii, N.; Hashmi, A. S. K.; Ohno, H. Org. Lett. 2015, 17, 604.(b) Zhu, L.; Yu, Y.; Mao, Z.; Huang, X. Org. Lett. 2015, 17, 30.
[9] Dateer, R. B.; Pati, K.; Liu, R.-S. Chem. Commun. 2012, 48, 7200.
[10] (a) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941 (in Chinese).(赵巾巾, 高文超, 常宏宏, 李兴, 刘强, 魏文珑, 有机化学, 2014, 34, 1941.) (b) Shen, S.; Xu, X.; Ji, S. Chin. J. Org. Chem. 2009, 29, 806 (in Chinese). (沈舒苏, 徐小平, 纪顺俊, 有机化学, 2009, 29, 806.)(c) Zhou, Y.; Yan, P.; Li, G.; Chen, Z. Chin. J. Org. Chem. 2009, 29, 1719 (in Chinese). (周颖, 闫鹏飞, 李光明, 陈正军, 有机化学, 2009, 29, 1719.)(d) Zhang, Z.; Liu, Q. Prog. Chem. 2006, 18, 270 (in Chinese). (张占辉, 刘庆彬, 化学进展, 2006, 18, 270.)(e) Wang, H.-S.; Miao, J.-Y.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 615 (in Chinese). (王宏社, 苗建英, 赵立芳, 有机化学, 2005, 25, 615.) (f) Ren, Y.-M.; Cai, C.; Yang, R.-C. RSC Adv. 2013, 3, 7182.(g) Mphahlele, M. J. Molecules 2009, 14, 4814.
[11] Métayer, B.; Compain, G.; Jouvin, K.; Martin-Mingot, A.; Bachmann, C.; Marrot, J.; Evano, G.; Thibaudeau, S. J. Org. Chem. 2015, 80, 3397.
[12] (a) Smith, D. L.; Goundry, W. R. F.; Lam, H. W. Chem. Commum. 2012, 48, 1505. (b) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170. (c) Zhang, Y.; Hsung, R. P.; Tacey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 7, 1151.
/
| 〈 |
|
〉 |
