Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

doi:10.6023/cjoc201401019

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1218-1221.DOI: 10.6023/cjoc201401019 Previous Articles Next Articles

Notes

邻羟基芳香N-叔丁基亚磺酰亚胺的微波合成研究

赵云辉, 任新芳, 刘汉文, 唐子龙

a. 湖南科技大学化学化工学院湘潭 411201;
b. 理论化学与分子模拟省部共建教育部重点实验室湘潭 411201

收稿日期:2014-01-11 修回日期:2014-02-12 发布日期:2014-03-10
通讯作者: 赵云辉, 刘汉文 E-mail:zhao_yunhui@163.com;hwyliu@126.com
基金资助:
国家自然科学基金（No. 21372070）、湖南省科学基金课题（No. 11JJ3016）和湖南省教育厅基金（No. B31314）资助项目.

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

Zhao Yunhui, Ren Xinfang, Liu Hanwen, Tang Zilong

a. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;
b. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education of China, Human University of Science and Technology, Xiangtan 411201, China

Received:2014-01-11 Revised:2014-02-12 Published:2014-03-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372070), the Science Foundation of Hunan Province (No. 11JJ3016) and the Hunan Provincial Education Office Scientific Research Foundation Project (No. B31314).

Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new (R,E)-N-(2-hydroxybenzylidene)-tert-butyl-sulfinamides (3) were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO₄/PhMe or Cs₂CO₃/CH₂Cl₂. And the results show that the KHSO₄/PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs₂CO₃/CH₂Cl₂reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by¹H NMR, ¹³C NMR, IR and HRMS.

Key words: microwave irradiation, chiral imine, (R)-tert-butylsulfinamide, salicylaldehyde

Cite this article

Zhao Yunhui, Ren Xinfang, Liu Hanwen, Tang Zilong. Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation[J]. Chin. J. Org. Chem., 2014, 34(6): 1218-1221.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kells, K. W.; Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666.

[2] Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268.

[3] Chen, B. L.; Wang, B.; Lin, G. Q. J. Org. Chem. 2010, 75, 941.

[4] Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.

[5] Lefebvre, I. M.; Evans, S. A. J. Org. Chem. 1997, 62, 7532.

[6] Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518.

[7] Voituriez, A.; Pérez-Luna, A.; Ferreira, F.; Botuha, C.; Chemla, F. Org. Lett. 2009, 11, 931.

[8] González-Gómez, J.; Foubelo, F.; Yus, M. J. Org. Chem. 2009, 74, 2547.

[9] Lee, A., Ellman, J. A. Org. Lett., 2001, 3, 3707.

[10] Procopiou, G.; Lewis, W.; Harbottle, G.; Stockman, R. A. Org. Lett. 2013, 15, 2030.

[11] Voituriez, A.; Ferreira, F.; Chemla, F. J. Org. Chem. 2007, 72, 5358.

[12] Davis, F. A.; Melamed, J. Y.; Sharik, S. S. J. Org. Chem. 2006, 71, 8761.

[13] Fei, Z. B.; Kong, W. Y.; Wang, H. M. Peng, J. B.; Sun, F.; Yin, Y. Y.; Bajwa, J.; Jiang, X. L. Org. Process Res. 2012, 16, 1436.

[14] Meng, X. T.; Huang, Y.; Chen R. Y. Org. Lett. 2009, 11, 137.

[15] Li, Q. B.; Zhou, F. T.; Liu, Z. G.; Li, X. F.; Zhu, W. D.; Xie, J. W. J. Org. Chem. 2011, 76, 7222.

[16] Tang, Z. L.; Chen, W. W.; Zhu, Z. H.; Liu, H. W. J. Heterocycl. Chem. 2011, 48, 255.

[17] Zhang, W. L.; Zhu, C. L.; Wang, D. X.; Yao, B. J.; Li, X. N. Chem. J. Chin. Univ. 2013, 34, 1794 (in Chinese).

(张文利, 朱春莉, 王登霞, 姚丙建, 李晓娜, 鲁在君, 高等学校化学学报, 2013, 34, 1794.)

[18] Chen, C. Y.; Andreani, T.; Li, H. M. Org. Lett. 2011, 13, 6300.

[19] Cimarelli, C.; Palmieri, G.; Volpini, E. Tetrahedron 2001, 57, 6089.

[20] Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361.

[21] Palmieri, G. Eur. J. Org. Chem. 1999, 805.

[22] Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. Synth. Commun. 2012, 42, 1372.

邻羟基芳香N-叔丁基亚磺酰亚胺的微波合成研究

Study on Synthesis of ortho-Hydroxyl Aromatic N-tert-Butylsulfinyl Imines under Microwave Irradiation

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xie Tinghui, Jiang Xiaoying, Mi Zhisheng, Li Xue, Xu Xiaohe, Bai Renren, Shuai Qi, Xie Yuanyuan. Iron/O₂-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3294-3298.
[2]	Zong Chaoyang, Gu Huiwen, Zhang Lijie, Jin Yudong, Sun Yaquan. Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives [J]. Chin. J. Org. Chem., 2018, 38(5): 1165-1171.
[3]	Qu Renyu, Chen Nian, Liu Yuchao, Chen Qiong, Yang Guangfu. An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation [J]. Chin. J. Org. Chem., 2017, 37(5): 1266-1272.
[4]	Huang Yaobing, Yang Tao, Liu Anfeng, Zhou Xincheng, Pan Hui. Microwave-Assisted Alcoholysis of Cellulose to Methyl Levulinate Catalyzed by SnCl₄/H₂SO₄ [J]. Chin. J. Org. Chem., 2016, 36(6): 1438-1443.
[5]	Zhang Bianxiang, Yang Lihua, Shi Ruixue, Kang Yongqiang. Synthesis of Heterocyclic Aromatic Sulfides under Microwave Irradiation [J]. Chin. J. Org. Chem., 2016, 36(2): 352-357.
[6]	Zhang Rui, Pan Jinhuan, Wu Qiongyou. Copper Mediated One-Pot Multi-Component Synthesis of 3-Substitued Isoquinolines [J]. Chin. J. Org. Chem., 2016, 36(12): 2906-2911.
[7]	Zhu Jihua, Zheng Xudong, Guo Guozhe, Zhang Yuquan, Wu Bowan. Microwave-Assisted Synthesis of Asymmetrical 1,5-Disubstituted Carbonohydrazide and Crystal Structure [J]. Chin. J. Org. Chem., 2015, 35(9): 1975-1980.
[8]	Feng Junna, Li Xiaohui, Shao Jie, Zhu Mo, Li Yan, Chen Hua, Li Xiaoliu. Microwave Assisted Synthesis and Anti-HIV-RT Activity of Diaryl Benzo[1,3]thiazin-4-ones [J]. Chin. J. Org. Chem., 2015, 35(6): 1370-1374.
[9]	Wang Juxian, Lin Wei, Liu Hongtao, Hu Minghua, Feng Xian, Ren Jinfeng, Huang Zhibin, Shi Daqing. An Efficient Synthesis of Coumarino[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives Catalyzed by Silica Sulfuric Acid under Microwave Irradiation [J]. Chin. J. Org. Chem., 2015, 35(4): 927-933.
[10]	Li Yingjun, Shi Xiangling, Gao Lixin, Jin Kun, Sheng Li, Wu Jianghong, Peng Lina, Li Jia. Synthesis, Characterization and Biological Activities of 3,5,6-Trisubstituted-1,2,4-triazine Derivatives [J]. Chin. J. Org. Chem., 2015, 35(1): 191-199.
[11]	Chen Hua, Huang Changjun, Zhu Mo, Li Xiaoliu. Synthesis and Anti-HIV-RT Activity of Novel Thiazolindin-4-one Derivatives Possessing Hydrophilic Groups [J]. Chin. J. Org. Chem., 2014, 34(4): 756-760.
[12]	Yang Jiaqiang, Ma Jun, Che Wanli, Li Minggang, Li Gang, Song Baoan. Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives [J]. Chin. J. Org. Chem., 2014, 34(12): 2566-2571.
[13]	Tong Guangjin, Fan Wei, Jiang Bo. Three-Component Synthesis of Oxazolo[3,4-b]quinoline Derivatives [J]. Chin. J. Org. Chem., 2013, 33(12): 2578-2582.
[14]	Sun Hongshun, Wang Jianqiang, Guo Cheng, Shen Linjiang. Synthesis of 5-Amino-2-oxo-7-aryl-2,3,4,7-tetrahydro-1,3-thiazolo[4,5-b]pyridine-6-carboxamide Derivatives under Microwave Irradiation [J]. Chin. J. Org. Chem., 2013, 33(10): 2220-2225.
[15]	Li Yingjun, Shao Xin, Gao Lixin, Jin Kun, Sheng Li, Luo Tongchuan, Yu Yang, Li Jia. Microwave-Assisted Synthesis and Biological Activities of 3,6-Disubstituted-1,2,4-triazine Derivatives [J]. Chin. J. Org. Chem., 2013, 33(10): 2178-2185.