Dissertation > Excellent graduate degree dissertation topics show

Study on the Copper-Catalyzed One-Pot Synthesis of Nitrogen-Containing Heterocyclic Compounds

Author: ZhouBingWei
Tutor: GaoJianRong；JinHongWei
School: Zhejiang University of Technology
Course: Organic Chemistry
Keywords: copper(Ⅰ) iodide cross-coupling reaction multicom- ponent reaction one-pot procedure
CLC: O626
Type: Master's thesis
Year: 2011
Downloads: 159
Quote: 0
Read: Download Dissertation

Abstract


Copper-catalyzed cross-coupling reaction serves the new strategy for the formation of C-C, C-N and C-O bonds. The novel one-pot procedure for multicomponent coupling reaction is carried out in dispensing with further purification of the intermediates and simplifying the procedure. It has been highlighted as one of the research frontiers in organic chemistry. In the dissertation copper-catalyzed Ullmann-type coupling reaction and multicomponent reaction have been studied. Twenty-five new nitrogen-containing heterocyclic compounds were synthesized in one-pot procedure. The synthetic topic is novel, which has its great originality and research value.The copper-catalyzed one-pot synthesis of benzimidazo[1,2-a] quinolines was studied starting from 2-（1H-benzo[d]imidazol-2-yl） acetonitrile and 2-bromobenzaldehyde. The possible mechanism was studied. 2-（1H-benzo[d]imidazol-2-yl） acetonitrile reacts with 2-bromo- benzaldehyde known as Knoevenagel condensation followed by an intramolecular C-N coupling reaction. The influence of solvent, ligand, base and temperature on the reaction had been investigated. The reaction was carried out in the yield of 84% with 5% mol CuI, 20% mol 1,10-phenanthroline and 2.0 eq. K2CO3 in dioxane under 90℃. The scope of substrates was subsequently examined. Unsubstituted benzimidazo [1,2-a]quinoline was synthesized in the yield of 90%.The copper-catalyzed three-component reaction in one-pot procedure was studied starting from acetylene, p-toluenesulfonyl azide and 2-bromoallyamine. The possible mechanism was studied. The [3+2] cycloaddition between terminal alkynes and azides is conducted in the presence of CuI and TEA. The ketenimine intermediate is attacked by 2-bromoallyamine to give N-Sulfonylamidine derivatives, followed by an intramolecular C-N coupling reaction. In order to screen the optimal reaction condition, the influence of solvent, temperature, ligand and base was investigated on the sequential C-N coupling reaction. The reaction was carried out in the yield of 60% with 10% mol CuI, 20% mol N,N’-dimethylethane-1,2-diamine and 2.0 eq. K2CO3 in the mixed solvents of CH3CN and DMSO （the volume ratio is 2∶1）. The scope of substrates was subsequently examined.25 new compounds synthesized were characterized by 1H-NMR, 13C-NMR and HRMS analysis. Copper-catalyzed one-pot synthesis of nitrogen-containing heterocyclic compounds shows some advantages such as simple experimental procedure, mild reaction condition, moderate to good yield and superior to step economy.

Related Dissertations

  1. 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
  2. Synthesis of Chiral N-aryl-α-amino Acids by Pd Catalyzed Couplings of Aryl Chloride,O643.32
  3. Synthesis of 2-Pyrones Via Palladium-Catalyzed Selective Cross-Coupling Reactions and Study on Copper-Catalyzed Chan-Lam Cross-Coupling Reactions,O643.32
  4. Research on Ullmann Reactions Catalyzed by Cu(Ⅱ),O643.32
  5. Studies on the Palladium or Copper-Catalyzed Cross Coupling Reaction,O643.32
  6. Copper -catalyzed C-N coupling reaction and the C = N Reaction,O643.32
  7. Preparation of Nano-CuI and the Application for Cross-coupling Reaction,O643.32
  8. Palladium-Catalyzed Amidation Using Tert-Butyl Carbamate and Hiyama Cross-Coupling Reaction of 2-Trimethylsilylpyridine with Aryl Bromindes,O643.32
  9. Oxygen-functionalizing of Aromatic C-H Bond,O621.13
  10. Synthesis and Characterization of Hyperbranched Polyesters with Pyromellit-Tetra-Diethanol Amine as the Central Core,O631.3
  11. Synthesis and Application of the new N-heterocyclic carbene palladium complexes,O627.8
  12. Synthesis of Functionalized Phosphine Ligands and Their Application to Cross-coupling Reactions,O643.36
  13. Carbene Analogs and Their Cycloaddition,O643.32
  14. The Synthesis of Naphthalene Boronic Acids and Derivatives,O627.8
  15. Studies on the Sonogashira Coupling Reaction Catalyzed by Copper-free,O643.32
  16. Synthesis of Dibenzo-fused Seven-member Nitrogen Heterocycle,O626.5
  17. Applications of Hydromagnesiation Reaction of Alkynes in Stereoselective Synthesis of Alkenes,O621.2
  18. Synthesis and Applications of (E)-α-stannyl-α, β-unsaturated Esters in Highly Selective Synthetic Reactions,O621.2
  19. Studies on the Applications of (E)-α-Bromovinylselenides and (Z)-α-Silylvinyl Grignard Reagents in Stereoselective Synthesis of Substituted Alkenes,O621.25
  20. Synthesis of (E)-α-Iodovinyltellurides and (Z)-α-Arylsulfenylvinyltellurides and Their Applications in Highly Selective Synthetic Reactions,O621.3
  21. α- halogenated vinyl stannane synthesis reaction at high selectivity in the application and (E)-β- arylthio vinyl selenides stereoselective synthesis,O621.3

CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
© 2012 www.DissertationTopic.Net  Mobile