Chinese Journal of Organic Chemistry >
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).
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
Meng Tuanjie , Chen Rongxiang , Liu Lantao , Wang Tao , Liu Xinming , Zhao Wenxian . Facile Synthesis of 1,3,5-Oxadiazin-2-one Derivatives through Three-Component One-Pot Cyclization of Molecular Iodine, Ynamides and Nitriles[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2108 -2113 . DOI: 10.6023/cjoc201505048
[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.
/
| 〈 |
|
〉 |
