Facile Synthesis of 1,3,5-Oxadiazin-2-one Derivatives through Three-Component One-Pot Cyclization of Molecular Iodine, Ynamides and Nitriles

doi:10.6023/cjoc201505048

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2108-2113.DOI: 10.6023/cjoc201505048 Previous Articles Next Articles

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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

孟团结^a, 陈荣祥^a,b, 刘澜涛^a, 王涛^a, 刘新明^a, 赵文献^a,b

a 商丘师范学院化学化工学院有机新材料合成重点实验室商丘 476000;
b 郑州大学化学与分子工程学院郑州 450052

收稿日期:2015-05-30 修回日期:2015-06-10 发布日期:2015-06-19
通讯作者: 刘澜涛, 赵文献 E-mail:liult05@iccas.ac.cn;zhwx5126@163.com
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

Meng Tuanjie^a, Chen Rongxiang^a,b, Liu Lantao^a, Wang Tao^a, Liu Xinming^a, Zhao Wenxian^a,b

a Key Laboratory of New Organic Materials synthesis, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000;
b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Received:2015-05-30 Revised:2015-06-10 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).

1. Facile Synthesis of 1,3,5-Oxadiazin-2-one Derivatives through Three-Component One-Pot Cyclization of Molecular Iodine, Ynamides and Nitriles.PDF(783KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2015, 35(10): 2108-2113.

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[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.

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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

Facile Synthesis of 1,3,5-Oxadiazin-2-one Derivatives through Three-Component One-Pot Cyclization of Molecular Iodine, Ynamides and Nitriles

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