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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Trimethylsilyl Isothiocyanate (TMSNCS)

Rosana Helena C. N. Freitas A
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A LASSBio, B16, subsolo, CCS, Universidade Federal do Rio de Janeiro, 21941-902, Rio de Janeiro, Brazil. Email: freitasrh@yahoo.com.br




Rosana Helena C. N. Freitas received her MSc degree in Chemistry (2013) from Federal University of Rio de Janeiro. Now she’s DSc student in Chemistry at the same university under the guidance of Prof. Carlos A. M. Fraga and Edson F. Silva. Her work involves heterocycles synthesis design as anti-trypanosomal prototypes.

Australian Journal of Chemistry 69(8) 928-929 https://doi.org/10.1071/CH16057
Submitted: 31 January 2016  Accepted: 16 March 2016   Published: 15 April 2016

Abstract

The versatility of trimethylsilyl isothiocyanate (TMSNCS) as a reagent is impressive, especially in heterocycle synthesis. TMSNCS is also commonly used in reactions of thiocyanation and isothiocyanation. The advantages of TMSNCS are moderated toxicity, chemical stability, high tolerance with other functional groups, and ease of handling. This paper highlights a selection of many different and recently reported types of reactions that this reagent is able to promote.


References

[1]  Z. Liang, F. Wang, P. Chen, G. Liu, Org. Lett. 2015, 17, 2438.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXntFGitr8%3D&md5=46932612408c25b9364ad53d8d6589d3CAS | 25908571PubMed |

[2]  N. Sun, L. Che, W. Mo, B. Hu, Z. Shen, X. Hu, Org. Biomol. Chem. 2015, 13, 691.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvFSmsbnF&md5=36b324b4370f9925002f153fe82b2a3cCAS | 25514847PubMed |

[3]  M. M. Mane, D. M. Pore, Tetrahedron Lett. 2014, 55, 6601.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhslOrtb7O&md5=22220305ae4f91067a944ba2921bfc02CAS |

[4]  V. Golubev, F. Zubkov, M. Krasavin, Tetrahedron Lett. 2013, 54, 4844.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFemtbvF&md5=a97de6800bc035b271ffdecbfa2ebc10CAS |

[5]  D. R. Guda, T. Wang, H. M. Cho, M. E. Lee, Tetrahedron Lett. 2012, 53, 5238.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtF2hsr%2FK&md5=52c9a09bbccb96788b6d411fcd21247aCAS |

[6]  D. R. Guda, H. M. Cho, M. E. Lee, RSC Adv. 2013, 3, 6813.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXmtlait7w%3D&md5=567ae33f10ef239f97f6e96e2b5e3edcCAS |

[7]  D. R. Guda, H. M. Cho, M. E. Lee, RSC Adv. 2013, 3, 7684.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXntVyqsbs%3D&md5=a2b3b9cb61c533d9dfc301bef22058a4CAS |

[8]  R. B. Ruggeri, L. Buckbinder, S. W. Bagley, P. A. Carpino, E. L. Conn, M. S. Dowling, D. P. Fernando, W. Jiao, D. W. Kung, S. T. M. Orr, Y. Qi, B. N. Rocke, A. Smith, J. S. Warmus, Y. Zhang, D. Bowles, D. W. Widlicka, H. Eng, T. Ryder, R. Sharma, A. Wolford, C. Okerberg, K. Walters, T. S. Maurer, Y. Zhang, P. D. Bonin, S. N. Spath, G. Xing, D. Hepworth, K. Ahn, A. S. Kalgutkar, J. Med. Chem. 2015, 58, 8513.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhslOrt7%2FK&md5=2209820a77c0d1795269d895358fdaccCAS | 26509551PubMed |

[9]  A. Schulz, A. Villinge, Chem. – Eur. J. 2010, 16, 7276.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXotVertrs%3D&md5=bc43ca31177532f4b4afea8aa79cf60eCAS | 20461830PubMed |

[10]  (a) For examples see: R. C. Cambie, P. F. Davis, P. S. Rutledge, P. D. Woodgate, Aust. J. Chem. 1984, 37, 2073.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXisVWjtg%3D%3D&md5=cc704f4d8210f82f8383c2f9a8a20166CAS |
      (b) W. Sufang, W. Shaobing, X. Yongshen, Synth. Commun. 2005, 35, 1271.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) N. V. Zyk, A. Y. Gavrilova, O. A. Mukhina, A. A. Borisenko, O. B. Bondarenko, N. S. Zefirov, Russ. Chem. Bull. 2010, 59, 1771.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  S. Nakamura, M. Ohara, M. Koyari, M. Hayashi, K. Hyodo, N. R. Nabisaheb, Y. Funahashi, Org. Lett. 2014, 16, 4452.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtlaisrbK&md5=b41349062e16a6762df87297979ece0fCAS | 25105534PubMed |

[12]  W. Zhang, J. Ai, D. Shi, X. Peng, Y. Ji, J. Liu, M. Geng, Y. Li, Molecules 2014, 19, 2655.
         | Crossref | GoogleScholarGoogle Scholar | 24566328PubMed |