Synthesis of vinylidene-2-imino(iminium)1,3-dithiolanes via halocyclization reaction of S-propargyl dithiocarbamates

Dithiocarbamates have variety of applications in organic synthesis. In addition to their pharmaceutical properties and their applications in synthesis of pesticides, these compounds can act as important intermediates in the synthesis of other important organic compounds. For instance, in recent years, dithiocarbamates played an important role in the synthesis of 2-imino(iminium)1,3-dithiolane rings4. These sulfur heterocycles are of great importance and can be further used for protection of crop plants from the action of herbicides without reducing the herbicidal effectiveness against weeds. In this project, S-propargyl dihtiocarbamate (3,5) intermediates were synthesized from the reaction of amines, CS2 and propargyl bromide 2. In the next step, vinylidene 2-imino(iminium)1,3-dithiolanes (4,6) were prepared in a short reaction time by the iodocyclization reaction of S-propargyl dithiocarbamates (3,5) with I2, under a mild reaction condition.

Keywords:

Dithiocarbamates , 1 , 3-dithiolanes