Dissertation > Excellent graduate degree dissertation topics show

Study on Synthesis of2-amine-substituted Aryl Sulfides with Benzothiazole in Aqueous Media

Author: QiHongXia
Tutor: FengYiSi; XuHuaJian
School: Hefei University of Technology
Course: Biochemical Engineering
Keywords: copper catalyzed C-S cross-coupling benzothiazole 2-aminophenyl sulphide
CLC: O621.36
Type: Master's thesis
Year: 2012
Downloads: 34
Quote: 0
Read: Download Dissertation


Since Migita and coworkers firstly reported palladium-catalyzed C-Scross-coupling reaction, much research had been putted on the carbon-sulfur bondforming reaction. The construction of amine-substituted aryl sulfides is an importanttool in biological, pharmaceutical and material aspects. For example, various sorts ofamine-substituted aryl sulfides are used in different kinds of pharmaceuticalcompounds which have been shown to exhibit anti-inflammatory, antitumor,antiprotozoal, antipsychotic, and antidepressant agent properties. These methods havebecome common and reliable methods in application, but still have some limitations,including harsh conditions, multi-step reactions, and expensive raw materials. So thedesign of a “green” chemical protocol is necessary. In the past few decades theenvironmentally-benign and economic chemical processes have attracted broadattentions, both the use of ligand-free catalytic systems and water as solvent are stillthe perfect target. Because this solvent has many valuable features, such asnon-toxicity, low cost, availability and greater chemoselectivity compared withorganic solvents. In this paper, we research the C-S coupling reaction based on usingwater as solvent.A novel synthetic method for2-aminophenyl sulphide derivatives ofbenzothiazole with aryl iodides was reported for the first time. The reactions werecatalyzed by a combination of ligand-free copper salt and tetrabutylammoniumhydroxide (acting as the base) using water as the solvent at50oC for12h. A varietyof aryl iodides underwent the C-S Cross-Coupling reaction with benzothiazolesmoothly to afford the corresponding products in good yield. This demonstrated thatthe universality of the reaction were very broad. Unfortunately, ArBr, ArCl and ArFcouldn’t react with benzothiazole in spite of doing many attempts. Only poor amountof the products were obtained for the aryl bromides with electron-withdrawingsubstituents. Both1-Methyl-1H-benzo[d]-imidazole and benzo[d]oxazole, which hassimilar chemical properties with benzothiazole, couldn’t react with aryl iodides in thiscatalyst system. In addition, we also research and state the possible mechanism of thereaction. The2-aminophenyl sulpho salts which enters the catalytic cycle was gotafter deprotonation of benzothiazole, ring-opened and hydrolysis process. The catalytic cycle is ordinary oxidative addition and reductive elimination process. Ofcourse, the mechanism and the further application of the reaction still needs furtherstudy.

Related Dissertations

  1. Theoretical study of carbazole derivatives,O626
  2. Benzothiazole - pyrimidine nucleoside hybrid body and pyrone and pyrimidine synthesis of bicyclic nucleoside,O626
  3. Design, Synthesis and Property Studies of Functionalized Crown Ethers,O621.3
  4. Synthesis of Benzothiazoles and Imidazoles Heterocyclic Compounds,O621.25
  5. The Coupling Reaction in the Synthesis of Trifluoromethyl Contained Compounds,O621.25
  6. Radar servo control based on CAN bus coordinated research,TN95
  7. Synthesis and Characterization of pyrazole the morpholine fluorescent compounds,O626.2
  8. Studies on the Clean Synthesis of 2-substituted Benzothiazoles,O621.25
  9. The Study of 3-sulfenylindoles and 2-aminobenzothiazoles Synthetic Methods,O621.25
  10. Form C-S Bond by Tandem Reaction,O621.2
  11. Carbon-Nitrogen Bond Formation: Palladium-Catalyzed Synthesis of Chiral N-heteroaryl Amino Acids Via Cross-Coupling Reaction of Heteroaryl Halides with Amino Acids,O643.32
  12. Synthesis of Chiral N-aryl-α-amino Acids by Pd Catalyzed Couplings of Aryl Chloride,O643.32
  13. The Technology Research of Synthetize Dihydroxyacetone,TQ224.223
  14. Synthesis and Characterization of Pyrazoline Fluorescent Compounds Containing Pyrimidyl,O626.2
  15. Synthesis and Fluorescence Properties of Pyrazole Oxadiazole and Pyrazole Benzothiazole Oxadiazole Derivatives,O626.2
  16. Selective Synthesis of Alkenyl Sulfides and Benzothiazole Derivatives,O621.25
  17. Rubber vulcanization accelerator CBS Synthesis Process Improvement,TQ330.385
  18. The Studies of Synthesis, Characterization and Photophysical Properties of New Type Iridium Complexes,O641.4
  19. Novel coordination polymer organic electroluminescent materials design synthesis and properties of,O631.3
  20. Benzothiazole and quinoxaline compounds Synthesis of environmentally friendly,O626
  21. Synthesis of Red-emitting Irdium Complexes and Their Electrophosphorescence Devices,TN383.1

CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry > Heavy organic synthesis or catalytic organic synthesis
© 2012 www.DissertationTopic.Net  Mobile