629-12-9Relevant articles and documents
A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur
Nickisch,Conen,Gabrielsen,Meier
, p. 3134 - 3142 (2021/01/28)
Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is
Synthesis and biological activity of diisothiocyanate-derived mercapturic acids
Grzywa, Renata,Winiarski, ?ukasz,Psurski, Mateusz,Rudnicka, Agata,Wietrzyk, Joanna,Gajda, Tadeusz,Oleksyszyn, Józef
supporting information, p. 667 - 671 (2016/01/09)
This Letter deals with new non-natural diisothiocyanates, their mercapturic acid derivatives - conjugated with N-acetylcysteine as well as their antiproliferative activity towards human colon cancer cell lines and their inhibitory potency towards histone deacetylase activity. The activity of analysed isothiocyanates is not significantly different than their N-acetylcysteine conjugates. In comparison to simple mono-isothiocyanate analogues, aliphatic diisothiocyanates and their conjugates are much more active than the simple presence of two isothiocyanate functionalities could indicate.
A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate
Munch, Henrik,Hansen, Jon S.,Pittelkow, Michael,Christensen, J?rn B.,Boas, Ulrik
, p. 3117 - 3119 (2008/09/20)
Alkyl and aryl amines are converted smoothly to the corresponding isothiocyanates via the dithiocarbamates in good to excellent yields using di-tert-butyl dicarbonate (Boc2O) and 1-3 mol % of DMAP or DABCO as catalyst. As most of the byproducts are volatile, the work-up involves simple evaporation of the reaction mixture.