Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant

doi:10.6023/cjoc201512038

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1375-1381.DOI: 10.6023/cjoc201512038 Previous Articles Next Articles

Articles

2,3-二氯-5,6-二氰基-1,4-苯醌促进的3,4-二氢嘧啶硫酮的氧化偶联反应合成1,2-二嘧啶基二硫醚

王刚^a, 郭燕^a, 吕颖^a,b, 王喜存^a, 权正军^a

a 西北师范大学化学化工学院兰州 730070;
b 兰州市第四十六中学兰州 730030

收稿日期:2015-12-25 修回日期:2016-01-21 发布日期:2016-02-18
通讯作者: 权正军, 王喜存 E-mail:quanzhengjun@hotmail.com;wangxicun@nnwu.edu.cn
基金资助:
国家自然科学基金(Nos.21362032,21362031)资助项目.

Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant

Wang Gang^a, Guo Yan^a, Lü Ying^a,b, Wang Xicun^a, Quan Zhengjun^a

aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
b Lanzhou No. 46 Middle School, Lanzhou 730030

Received:2015-12-25 Revised:2016-01-21 Published:2016-02-18
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362032, 21362031).

1. Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant.PDF(1790KB)

Abstract

The oxidative coupling and aromatization of 3,4-dihydropyrimidin-2-thiones to produce 1,2-di(pyrimidin-2-yl)- disulfides by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant at room temperature under an air atmosphere are reported. Compared with the reported procedures, this method has obvious advantages at mild reaction conditions including lower reaction temperature and shorter reaction time with higher yields of products.

Key words: 3,4-dihydropyrimidin-2-thiones, 1,2-di(pyrimidin-2-yl) disulfides, DDQ, oxidative coupling

Cite this article

Wang Gang, Guo Yan, Lü Ying, Wang Xicun, Quan Zhengjun. Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant[J]. Chin. J. Org. Chem., 2016, 36(6): 1375-1381.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Arterburn, J. B.; Perry, M. C.; Nelson, S. L.; Dible, B. R.; Holguin, M. S. J. Am. Chem. Soc. 1997, 119, 9309.
(b) Yang, J.; Stuart, M. A. C.; Kamperman, M. Chem. Soc. Rev. 2014, 43, 8271.
(c) Saito, G.; Swanson, J. A.; Lee, K. D. Adv. Drug Delivery Rev. 2003, 55, 199.
[2] (a) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Science 2002, 297, 590.
(b) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem. Int. Ed. 2002, 41, 898.
(c) Mandal, B.; Basu, B. RSC Adv. 2014, 4, 13854.
[3] (a) Sinha, P.; Kundu, A.; Roy, S.; Prabhakar, S.; Vairamani, M.; Sankar, A. R.; Kunwar, A. C. Organometallics 2001, 20, 157.
(b) Ranu, B. C.; Mandal, T. J. Org. Chem. 2004, 69, 5793.
(c) Baldovino-Pantaleón, O.; Hernández-Ortega, S.; Morales- Morales, D. Adv. Synth. Catal. 2006, 348, 236.
(d) Arisawa, M.; Suzuki, T.; Ishikawa, T.; Yamaguchi, M. J. Am. Chem. Soc. 2008, 130, 12214.
(e) Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem. Eur. J. 2009, 15, 3666.
(f) Gogoi, P.; Gogoi, S. R.; Kalita, M.; Barman, P. Synlett 2013, 873.
(g) Cheng, J.-H.; Yi, C.-L.; Liu, T.-J.; Le, C.-F. Chem. Commun. 2012, 48, 8440.
(h) Prasad, C. D.; Balkrishna, S. J.; Kumar, A.; Bhakuni, B. S.; Shrimali, K.; Biswas, S.; Kumar, S. J. Org. Chem. 2013, 78, 1434.
(i) Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066.
(j) Xu, X.-B.; Liu, J.; Zhang, J.-J.; Wang, Y.-W.; Peng, Y. Org. Lett. 2013, 15, 550.
[4] (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
(b) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
[5] (a) Kondo, T.; Uenoyama, S.-Y.; Fujita, K.-I.; Mitsudo, T.-A. J. Am. Chem. Soc. 1999, 121, 482.
(b) Singh, S.; Yadav, L. D. S. Org. Biomol. Chem. 2012, 10, 3932.
(c) Matsumoto, K.; Sanada, T.; Shimazaki, H.; Shimada, K.; Hagiwara, S.; Fujie, S.; Ashikari, Y.; Suga, S.; Kashimura, S.; Yoshida, J. Asian J. Org. Chem. 2013, 2, 325.
[6] (a) Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763.
(b) Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226.
(c) Du, H.-A.; Zhang, X.-G.; Tang, R.-Y.; Li, J.-H. J. Org. Chem. 2009, 74, 7844.
(d) Du, H.-A.; Tang, R.-Y.; Deng, C.-L.; Liu, Y.; Li, J.-H.; Zhang, X.-G. Adv. Synth. Catal. 2011, 353, 2739.
(e) Usugi, S.-I.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601.
(f) Hu, B.-L.; Pi, S.-S.; Qian, P.-C.; Li, J.-H.; Zhang, X.-G. J. Org. Chem. 2013, 78, 1300.
(g) Gonçalves, L. C. C.; Victória, F. N.; Lima, D. B.; Borba, P. M. Y.; Perin, G.; Savegnago, L.; Lenardão, E. J. Tetrahedron Lett. 2014, 38, 5275.
[7] (a) Grayson, E. J.; Ward, S. J.; Hall, A. L.; Rendle, P. M.; Gamblin, D. P.; Batsanov, A. S.; Davis, B. G. J. Org. Chem. 2005, 70, 9740.
(b) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
(c) Hyvl, J.; Srogl, J. Eur. J. Org. Chem. 2010, 2849.
(d) Zhang, S.; Qian, P.; Zhang, M.; Hu, M.; Cheng, J. J. Org. Chem. 2010, 75, 6732.
(e) Zhu, N.; Zhang, F.; Liu, G. J. Comb. Chem. 2010, 12, 531.
(f) Mitamura, T.; Iwata, K.; Ogawa, A. J. Org. Chem. 2011, 76, 3880.
(g) Deng, H.; Li, Z.; Ke, F.; Zhou, X. Chem. Eur. J. 2012, 18, 4840.
(h) Kundu, D.; Ahammed, S.; Ranu, B. C. Green Chem. 2012, 14, 2024.
(i) Mukherjee, N.; Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 11110.
[8] For selected examples, see: (a) Du, Y.; Yang, H.-C.; Xu, X.-L.; Wu, J.; Xu, Z.-K. ChemCatChem 2015, 7, 3822.
(b) Chauhan, D.; Kumar, P.; Joshi, C.; Labhsetwar, N.; Ganguly, S. K.; Jain, S. L. New J. Chem., 2015, 39, 6193.
(c) Bagi, N.; Kaizer, J.; Speier, G. O. RSC Adv. 2015, 5, 45983.
(d) Talla, A.; Driessen, B.; Straathof, N. J. W.; Milroy, L.-G.; Brunsveld, L.; Hessel, V.; Noël, T. Adv. Synth. Catal. 2015, 357, 2180.
[9] (a) Kappe, C. O. Tetrahedron 1993, 49, 6937.
(b) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
(c) Wan, J.-P.; Liu, Y. Synthesis 2010, 3943.
(d) Quan, Z.-J.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Chin. J. Org. Chem. 2009, 29, 876 (in Chinese). (权正军, 张彰, 达玉霞, 王喜存, 有机化学, 2009, 29, 876.)
[10] (a) Quan, Z.-J.; Lv, Y.; Wang, Z.-J.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Tetrahedron Lett. 2013, 54, 1884.
(b) Quan, Z.-J.; Lv, Y.; Jing, F.-Q.; Jia, X.-D.; Wang, X.-C. Adv. Synth. Catal. 2014, 356, 325.
(c) Du, B.-X.; Quan, Z.-J.; Da, Y.-X.; Zhang, Z.; Wang, X.-C. Adv. Synth. Catal. 2015, 357, 1270.
(d) Guo, Y.; Quan, Z.-J.; Da, Y.-X.; Zhang, Z. Wang, X.-C. RSC Adv. 2015, 5, 45479.
[11] Hayashi, M.; Okunaga, K.-i.; Nishida, S.; Kawamura, K.; Eda, K. Tetrahedron Lett. 2010, 51, 6734.
[12] (a) Lo, W. S.; Hu, W. P.; Lo, H. P.; Chen, C. Y.; Kao, C. L.; Vandavasi, J. K.; Wang, J. J. Org. Lett. 2010, 12, 5570.
(b) Vandavasi, J. K.; Hub, W.-P.; Chen, C.-Y.; Wang, J.-J. Tetrahedron 2011, 67, 8895.
[13] Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
[14] Wang, X. C.; Quan, Z. J.; Wang, F.; Wang, M. G.; Zhang, Z.; Li, Z. Synth. Commun. 2006, 36, 451.

[1]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[2]	Binghao Huo, Conghui Guo, Zhanhui Xu. Mn(acac)₃ Promoted Radical Oxidative Coupling Reaction of Enol Esters with Phosphites to Synthesize β-Ketophosphonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3989-3996.
[3]	Jianming Zhao, Jiashun Zhu, Jiabin Shen, Yilan Zhang, Wanmei Li. Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2940-2946.
[4]	Junfeng Qian, Xiaoting Tian, Zhong Wu, Jie Yao, Hui Wang, Weiyou Zhou. Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3668-3674.
[5]	Wei Chen, Qiang Liu. Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3414-3430.
[6]	Zhu Runyu, Zhai Min, Liu Shuang, Liu Xingtong, Wang Zhen, Ju Ruijun, Yu Xinhong. One-Pot Synthesis of N-Alkyl Indole from Indoline-2-carboxylic Acids and Alkyl Halides by 2,3-Dicyano-5,6-dichlorobenzoquinone (DDQ) Mediated Oxidative Decaboylative Aromatization [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2045-2050.
[7]	Yang Zhenhua, Zhu Jianan, Wen Caiyue, Ge Yingxiang, Zhao Shengyin. Recent Advances in Functionalization of Double Bond Based on Maleimides [J]. Chin. J. Org. Chem., 2019, 39(9): 2412-2427.
[8]	Chen Wei, Guo Renyu, Gong Jianxian, Yang Zhen. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction [J]. Chin. J. Org. Chem., 2019, 39(1): 238-248.
[9]	Liu Hong, Dong Huiru, An Rui, Tang Yu, Xu Kaitian, Zhang Yuanming. Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction [J]. Chin. J. Org. Chem., 2018, 38(8): 2008-2016.
[10]	Li Changsheng, Zou Yulong, Jia Changqing, Qin Zhaohai, Ma Yongqiang. Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole [J]. Chin. J. Org. Chem., 2018, 38(6): 1500-1506.
[11]	Xu Lige, Huang Yi, Liu Binggen, Niu Yunhong, Huo Xing. Progress in Oxidative Coupling Reaction of Olefins, Alkynes and Aromatic Hydrocarbons Catalyzed by Palladium [J]. Chin. J. Org. Chem., 2018, 38(4): 812-824.
[12]	Yan Yizhe, Cui Chang, Li Zheng. Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine [J]. Chin. J. Org. Chem., 2018, 38(10): 2501-2518.
[13]	Zhang Xiang, Cong Ying, Lin Guangyu, Guo Xuliang, Cao Yang, Lei Kunhua, Du Yunfei. Recent Advances of the Application of Organoiodine(Ⅲ) Reagents in the Construction of Heterocyclic Compounds [J]. Chin. J. Org. Chem., 2016, 36(11): 2513-2529.
[14]	Zhang Jian, Lu Qingquan, Liu Chao, Lei Aiwen. Recent Advances in Oxidative Coupling Reactions [J]. Chin. J. Org. Chem., 2015, 35(4): 743-759.
[15]	Zhang Ke, Xu Xiuhua, Qing Fengling. Recent Advances of Direct Trifluoromethylthiolation [J]. Chin. J. Org. Chem., 2015, 35(3): 556-569.

2,3-二氯-5,6-二氰基-1,4-苯醌促进的3,4-二氢嘧啶硫酮的氧化偶联反应合成1,2-二嘧啶基二硫醚

Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments