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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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
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author Zhang, Hao
Liu, Rui-Quan
Liu, Ke-Chang
Li, Qi-Bo
Li, Qing-Yang
Liu, Shang-Zhong
author_facet Zhang, Hao
Liu, Rui-Quan
Liu, Ke-Chang
Li, Qi-Bo
Li, Qing-Yang
Liu, Shang-Zhong
author_sort Zhang, Hao
collection PubMed
description 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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spelling pubmed-62711982018-12-27 A One-Pot Approach to Pyridyl Isothiocyanates from Amines Zhang, Hao Liu, Rui-Quan Liu, Ke-Chang Li, Qi-Bo Li, Qing-Yang Liu, Shang-Zhong Molecules Article 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. MDPI 2014-09-02 /pmc/articles/PMC6271198/ /pubmed/25185069 http://dx.doi.org/10.3390/molecules190913631 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Zhang, Hao
Liu, Rui-Quan
Liu, Ke-Chang
Li, Qi-Bo
Li, Qing-Yang
Liu, Shang-Zhong
A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title_full A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title_fullStr A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title_full_unstemmed A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title_short A One-Pot Approach to Pyridyl Isothiocyanates from Amines
title_sort one-pot approach to pyridyl isothiocyanates from amines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271198/
https://www.ncbi.nlm.nih.gov/pubmed/25185069
http://dx.doi.org/10.3390/molecules190913631
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