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The stereoselective synthesis of the tetrahydrothiopyranolr ,Y'-blindole skeletons via tandem reaction of indoline- r-thiones to Baylis-Hillman adduct acetates & Silica-Supported DABCO-tribromide: A New, Versatile and Recyclable Catalyst for the Chemoselective Oxidation of Sulfides to Sulfoxides and Oxidative Coupling of Thiols into Disulfides

Sobhani, Maryam | 2013

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 45215 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. We have reported a new and efficient synthesis of tetrahydrothiopyrano [2,3-b]indole skeletons via unique tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates. This protocol is a very mild and simple method for construction heterocycles in a one-step process. This is a convenient and diastereoselective synthesis of methyl 4-aryl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole-3-carboxylate systems in the presence of K2CO3 in acetonitrile. The major benefits of the current study are the one-pot procedure, high yields and diastereoselectivity, short reaction times and the similarity of the products to the biologically active moieties.
    In addition 1, 4-diazabicyclo [2.2.2] octane (DABCO) tribromide immobilized on silica has been introduced as a versatile and recyclable catalyst for the preparation of sulfoxides from sulfides, respectively. The supported catalyst recovered and reused four times without significant loss of activity. The reaction procedure is mild and corresponding products obtained in high yields
  9. Keywords:
  10. Tetrahydropyrano [2,3-b]Indol ; Baylis-Hillman Addact Acetate Reaction ; Indoline-2-Thion ; Tandem Reaction ; Sulfoxides ; Sulfide Oxidation ; Silica Support, DABCO Tribromide Catalysis

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