Improvement of the Synthesis of Isothiocyanates

doi:10.6023/cjoc201503026

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1999-2003.DOI: 10.6023/cjoc201503026 Previous Articles Next Articles

Notes

异硫氰酸酯的合成改进

李正义, 石嵩, 庄跃, 郑崇谦, 张金龙, 孙小强

常州大学石油化工学院江苏省绿色催化材料与技术重点实验室常州 213164

收稿日期:2015-03-18 修回日期:2015-04-16 发布日期:2015-05-14
通讯作者: 孙小强 E-mail:sunxiaoqiang@yahoo.com
基金资助:
国家自然科学基金(No. 21002009)、江苏省高校自然科学研究(Nos. 12KJA150002, 14KJA150002)、江苏省科技(BY2014037-01)和江苏省青蓝工程资助项目.

Improvement of the Synthesis of Isothiocyanates

Li Zhengyi, Shi Song, Zhuang Yue, Zheng Chongqian, Zhang Jinlong, Sun Xiaoqiang

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164

Received:2015-03-18 Revised:2015-04-16 Published:2015-05-14
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21002009), the Major Program for the Natural Science Research of Jiangsu Colleges and Universities (Nos. 12KJA150002, 14KJA150002), the Scientific and Technological Project of Jiangsu Province (BY2014037-01), and the Qing Lan Project of Jiangsu Province.

1. Improvement of the Synthesis of Isothiocyanates.PDF(945KB)

Abstract

Isothiocyanates were prepared from the reactions of phenyl chlorothionoformate and various primary amines vis one-step or two-step process without additional base. The one-step process is good at highly active amines, while two-step approach is suitable for all kinds of amines. This method has many merits such as environment-friendly, easily available raw materials, low toxicity and convenient operation, which has a good application prospect in industry.

Key words: isothiocyanate, phenyl chlorothionoformate, primary amine, synthesis

Cite this article

Li Zhengyi, Shi Song, Zhuang Yue, Zheng Chongqian, Zhang Jinlong, Sun Xiaoqiang. Improvement of the Synthesis of Isothiocyanates[J]. Chin. J. Org. Chem., 2015, 35(9): 1999-2003.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Mukerjee, A. K.; Ashare, R. Chem. Rev. 1991, 91, 1.(b) Dobosz, M.; Wujec, M. Heterocycles 2002, 57, 1135.(c) Li, M.; Zhang, J. W.; Wen, L. R. Chin. J. Org. Chem. 2014, 34, 2478 (in Chinese).(李明, 张建薇, 文丽荣, 有机化学, 2014, 34, 2478.)(d) Liu, R. Y.; Yong, X.; Yang, X. D.; Yan, Y. C.; Lu, X. W.; Qu, J. Q. Chin. J. Org. Chem. 2014, 34, 561 (in Chinese). (刘瑞源, 勇雪, 杨小东, 严轶琛, 路新卫, 瞿金清, 有机化学, 2014, 34, 561.)
[2] (a) Fahey, J. W.; Talalay, P. Food Chem. Toxicol. 1999, 37, 973.(b) Fahey, J. W.; Zalcmann, A. T.; Talalay, P. Phytochemistry 2001, 56, 5. (c) Heckl, S.; Sturzu, A.; Regenbogen, M.; Beck, A.; Feil, G.; Gharabaghi, A.; Echner, H. Med. Chem. 2008, 4, 348. (d) Bommareddy, A.; Hahm, E-R.; Xiao, D.; Powolny, A. A.; Fisher, A. L.; Jiang, Y.; Singh, S. V. Cancer Res. 2009, 69, 3704.(e) Gupta, P.; Kim, B.; Kim, S.-H.; Srivastava S. K. Mol. Nutr. Food Res. 2014, 58, 1685.(f) Gupta P.; Wright, S. E.; Kim, S.-H.; Srivastava, S. K. Biochim. Biophys. Acta 2014, 1846, 405.
[3] He, M. H.; Zhong, H.; Zhang, B. Y. Fine Spec. Chem. 2010, 18, 9 (in Chinese). (何谋海, 钟宏, 张宝元, 精细与专用化学品, 2010, 18, 9.)
[4] (a) Gao, Z.-L.; Liu, X.-L.; Liu, D.; Zhang, L.-Y. Agrochemicals 2009, 48, 322 (in Chinese).(高中良, 刘秀莲, 刘东, 张丽英, 农药, 2009, 48, 322.)(b) Liang, X. P. Jiangxi Plant Protection 2011, 34, 129 (in Chinese).(梁学平, 江西植保, 2011, 34, 129.)
[5] Dyer, E.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 777.
[6] (a) Larsen, C.; Stelliou, K.; Harpp, D. N. J. Org. Chem. 1978, 43, 337.(b) Larsen, C.; Harpp, D. N. J. Org. Chem. 1981, 46, 2465.(c) Kim, S.; Yi, K. Y. Tetrahedron Lett. 1985, 26, 1661.(d) Gottfried, R. Angew. Chem. 1966, 5, 963.
[7] (a) Yella, R.; Ghosh, H.; Murru, S.; Sahoo, S. K.; Patel, B. K. Synth. Commun. 2010, 40, 2083.(b) Jamir, L.; Ali, A. R.; Ghosh, H.; Chipem, F. A. S.; Patel, B. K. Org. Biomol. Chem. 2010, 8, 1674.(c) Nath, J.; Jamir, L.; Patel, B. K. Green Chem. Lett. Rev. 2011, 4, 1.(d) Jamir, L.; Alimenla, B.; Kumar, A.; Sinha, D.; Sinha, U. B. Synth. Commun. 2011, 41, 147.(e) Sun, N.; Li, B.; Shao, J.; Mo, W.; Hu, B.; Shen, Z.; Hu X. Beilstein J. Org. Chem. 2012, 8, 61.
[8] Zhang, X.; Lee, Y. K.; Kelley, J. A.; Burke, T. R., Jr. J. Org. Chem. 2000, 65, 6237.
[9] Chen, X.; Li, Z.; Sun, X.; Ma, H.; Chen, X.; Ren, J.; Hu, K. Synthesis 2011, 3991.
[10] Li, Z. Y,; Ma, H. Z.; Han, C,; Xi, H. T.; Meng, Q.; Chen, X.; Sun, X. Q. Synthesis 2013, 1667.
[11] Mays, J. R.; Roska, R. L. W.; Sarfaraz, S.; Mukhtar, H.; Rajski, S. R. ChemBioChem 2008, 9, 729.
[12] Butler, R. N.; Wallace, L. M. J. Chem. Soc., Perkin Trans. 1 2000, 4335.
[13] Hodgkins, J. E.; Reeves, W. P. J. Org. Chem. 1964, 29, 3098.
[14] Wang, R.; Dolman, S. J. J. Org. Chem. 2007, 72, 3969.
[15] Shan, W. G.; Bian, G. F.; Su, W. K.; Liang, X. R. Org. Prep. Proc. Int. 2004, 36, 283.
[16] Adam, W.; Bargon, R. M.; Bosio, S. G.; Schenk, W. A.; Stalke, D. J. Org. Chem. 2002, 67, 7037.
[17] Elderfield, R. C.; Short, F. W. J. Org. Chem. 1953, 18, 1092.

异硫氰酸酯的合成改进

Improvement of the Synthesis of Isothiocyanates

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.