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Synthesis 2017; 49(23): 5258-5262
DOI: 10.1055/s-0036-1588545
DOI: 10.1055/s-0036-1588545
paper
Base-Promoted Synthesis of O-Aryl/Alkyl N,N-Dimethylthiocarbamates Starting from Inexpensive and Environmentally Benign Disulfide
We thank the foundation support from National Natural Science Foundation of China (21302150), Hubei Provincial Department of Education (D20131501), Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012]1707, foundation of Chutian distinguished fellow from Hubei Provincial Department of Education, foundation of High-end Talent Cultivation Program from Wuhan Institute of Technology.
Weitere Informationen
Publikationsverlauf
Received: 29. Juni 2017
Accepted after revision: 19. Juli 2017
Publikationsdatum:
22. August 2017 (online)
Abstract
A series of O-aryl (alkyl) N,N-dimethylthiocarbamates were synthesized in good yields (70–77%) by reacting substituted phenols or alkyl alcohol with inexpensive, stable, and environmentally benign tetramethylthiuram disulfide (TMTD) in the presence of NaH. By avoiding use of the toxic and corrosive N,N-dialkylthiocarbamoyl chloride, the method provides a green and facile preparation for some important precursors of potentially biologically reactive compounds.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588545.
- Supporting Information
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References and Notes
- 1 Coel A. Mazur SJ. Fattah RJ. Bioorg. Med. Chem. Lett. 2002; 12: 767
- 2 Xue M. Long BH. Fairchild C. Bioorg. Med. Chem. Lett. 2000; 10: 1327
- 3 Harwood JL. Biochem. Soc. Trans. 1994; 22: 621
- 4 McElroy NR. Jurs PC. Morisseau C. Hammock BD. J. Med. Chem. 2003; 46: 1066
- 5 Lee SJ. Caboni P. Tomizawa M. Casida JE. J. Agric. Food Chem. 2004; 52: 95
- 6 Mizuno T. Junko T. Ogawa A. Tetrahedron 2003; 59: 1327
- 7 Yuck KO. Jie EP. Dae DS. J. Org. Chem. 2004; 69: 3150
- 8 Bowden SA. Burke JN. Gray F. McKown S. Moseley JD. Moss WO. Murray PM. Welham MJ. Young MJ. Org. Process Res. Dev. 2004; 8: 33
- 9 Kratky M. Volkova M. Novotna E. Trejtnar F. Stolarikva J. Vinsova J. Bioorg. Med. Chem. 2014; 22: 4073
- 10 Burns M. Lloyd-Jones GC. Moseley JD. Renny JS. J. Org. Chem. 2010; 75: 6347
- 11 Perkowski AJ. Cruz CL. Nicewicz DA. J. Am. Chem. Soc. 2015; 137: 15684
- 12 Rensburg J. Caryl K. Robinson A. Ross S. S. Afr. J. Chem. 2009; 62: 143
- 13 Zhao YW. Xie YJ. Xia CG. Huang HM. Adv. Synth. Catal. 2014; 356: 2471
- 14 Villemin D. Hachemi M. Lalaoui M. Synth. Commun. 1996; 26: 2461
- 15 Moseley JD. Sankey RF. Tang ON. Gilday JP. Tetrahedron 2006; 62: 4685
- 16 Kaupp G. Boy J. Schmeyers J. J. Prakt. Chem. 1998; 340: 346
- 17 Jen KY. Cava MP. J. Org. Chem. 1983; 48: 1449
- 18 Pudovik AN. Zh. Obshch. Khim. 1988; 58: 1489
- 19 Chiang GC. Res. Discl. 1992; 10: 342086
- 20 Liu M. Zeng MT. Xu W. Chang CZ. Liu X. Zhu H. Li YS. Dong ZB. J. Chem. Res. 2017; 47: 165
- 21 Xu W. Zeng MT. Liu M. Liu X. Chang CZ. Zhu H. Dong ZB. Chem. Lett. 2017; 46: 641
- 22 Xu W., Zeng M. T., Liu M., Liu X., Chang C. Z., Zhu H., Dong Z. B.; J. Sulfur Chem.; 2017, DOI: 10.1080/17415993.2017.1337771.
- 23 Chang CZ. Xu W. Zeng MT. Liu M. Liu X. Zhu H. Dong ZB. Synth. Commun. 2017; 47: 1262