A One-Pot Approach to Pyridyl Isothiocyanates from Amines

A one-pot preparation of pyridyl isothiocyanates (ITCs) from their corresponding amines has been developed. This method involves aqueous iron(III) chloride-mediated desulfurization of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide in the present of DA...

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Detalles Bibliográficos
Autores principales: Zhang, Hao, Liu, Rui-Quan, Liu, Ke-Chang, Li, Qi-Bo, Li, Qing-Yang, Liu, Shang-Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271198/
https://www.ncbi.nlm.nih.gov/pubmed/25185069
http://dx.doi.org/10.3390/molecules190913631
Descripción
Sumario:A one-pot preparation of pyridyl isothiocyanates (ITCs) from their corresponding amines has been developed. This method involves aqueous iron(III) chloride-mediated desulfurization of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide in the present of DABCO or sodium hydride. The choice of base is of decisive importance for the formation of the dithiocarbamate salts. This one-pot process works well for a wide range of pyridyl ITCs. Utilizing this protocol, some highly electron-deficient pyridyl and aryl ITCs are obtained in moderate to good yields.

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