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New Methods for the Synthesis of N,S‑Heterocycles and Dithiocarbamates Using Amine Derivatives and CS2

Goudarzi, Mehri | 2022

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 55187 (03)
  4. University: Sharif University of Technolog
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. In the first section, a novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using unltrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56-96% yields. This is the first report of Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization which lead to the preparation of the key structure of pyrrolidine.In the second section, an efficient and unprecedented green protocol for synthesis of N,S-heterocycles from styrenes and S-alkyl dithiocarbamates with high to excellent yields has been developed. The reaction of primary or secondary amines, CS2, and styrenes was carried out in water under catalytic amount of an inorganic base. All products were made by using of N-bromosuccinimide-H2O combination as a green and inexpensive reagent.In the third section, an efficient, green and one-pot three-component approach for the direct construction of pyrazoles-based dithiocarbamates via a C−H sulfenylation strategy mediated by molecular iodine is reported. Various pyrazolones derivatives containing electron-donating and electron-withdrawing functional groups were examined successfully in this protocol to afford pyrazoledithiocarbamates in moderate to excellent yields. In addition, the reaction of secondary amines, CS2, and 2-(nitromethylene)imidazolidine was carried out in ethanol as a green solvent without using transition metals or disulfiram
  9. Keywords:
  10. Dithiocarbamate ; Multicomponent Reaction ; Sulfur Containing Heterocycles ; Nitrogen Containing Heterocyclic Rings ; Diastereoselective ; Secondary Amine

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