Abstract
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.
Highlights
Isothiocyanates (ITCs) constitute an important class of natural products that are abundant in many cruciferous vegetables [1]
In Le Count’s work, iron(III) chloride has been proved to be effective for the decomposition of dithiocarbamate salts, but the preparation of N-pyridyldithiocarbamate salts was seldom investigated, so it became crucial for us to improve their preparation, because once the dithicarbamates were obtained, the desulfurylation step proceeded smoothly [13,16]
The effect of various bases was evaluated by performing the model reaction in tetrahydrofuran
Summary
Isothiocyanates (ITCs) constitute an important class of natural products that are abundant in many cruciferous vegetables [1]. ITCs have versatile biological activities, ranging from anticancer and chemoprotective properties [2,3,4] to agrochemical activities [5,6,7], and they are useful intermediates for the synthesis of various sulfur- and nitrogen-containing organic compounds [8], especially for heterocycles [9,10,11,12]
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