Four-Component Reaction for the Synthesis of Dithiocarbamates Starting from Cyclic Imines

• Published in: ACS combinatorial science Vol. 18; no. 8; pp. 456 - 460
• Main Authors: Schlüter, Torben, Ziyaei Halimehjani, Azim, Wachtendorf, Daniel, Schmidtmann, Marc, Martens, Jürgen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.08.2016; Amer Chemical Soc
• Subjects: Amines - chemistry; Carbon Disulfide - chemistry; Chemistry; Chemistry, Applied; Chemistry, Medicinal; Chemistry, Multidisciplinary; Chloroacetates - chemistry; Combinatorial Chemistry Techniques; Imines - chemistry; Life Sciences & Biomedicine; Molecular Structure; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Small Molecule Libraries - chemistry; Structure-Activity Relationship; Thiocarbamates - chemical synthesis; dithiocarbamates; carbon disulfide; one pot; multicomponent reaction; cyclic imines; ONE-POT SYNTHESIS; 3-COMPONENT REACTION; VULCANIZATION; MULTICOMPONENT REACTIONS; RING-CLOSING METATHESIS; CHEMISTRY; LACTAMS; INHIBITORS; PRECURSORS; WATER
• ISSN: 2156-8952; 2156-8944
• DOI: 10.1021/acscombsci.6b00029

An efficient one-pot, four-component reaction for the synthesis of dithiocarbamates using carbon disulfide, cyclic imines, acid chlorides, and commercially available primary or secondary amines has been developed by performing an acid chloride addition to a heterocyclic imine followed by subsequent nucleophilic substitution of in situ generated dithiocarbamic acid. With the aid of the newly developed and powerful multicomponent reaction, a direct route for the synthesis of 24 unknown dithiocarbamates in moderate to good yield under mild conditions is enabled.