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Copper-Catalyzed Synthesis of Nitrogen Heterocyclic Compound

Author: YangXiaoBo
Tutor: QiaoRenZhong
School: Beijing University of Chemical Technology
Course: Chemical Engineering and Technology
Keywords: Copper-catalyzed Ullmann reaction Indole Quinazoline
CLC: TQ25
Type: Master's thesis
Year: 2010
Downloads: 126
Quote: 0
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Abstract


Indoles and quinazoline compounds are very important to the two types of aza ring compounds, is a mother nucleus structure of many natural products and drugs . Synthesis methods of the past, these two types of compounds , however , has a raw material is difficult to obtain , under harsh conditions, the yield is not high disadvantage , so look for the raw materials are easily obtained under mild conditions and high yield synthesis method significant . Two synthesis of such compounds on the basis of the copper catalyzed Ullmann reaction . Made the following research : 1 : to establish a copper catalytic N-trifluoroacetyl- o- halogen aniline and β- cyano ester or malononitrile new method of synthesis of indole compounds . The catalyst is CuI (10mol%), the base is K2CO3 ( 2.0eq ) , the ligand is L-proline ( 20 mol %) , DMSO: H2O (1:1) as solvent , 60 ° C reaction . The raw materials of the catalytic system is simple and easy to get , under mild conditions, and high yield . Synthetically obtained product contains the functional group of the amino group and an ester group , can be used as intermediates of biologically active substance or a starting material for the synthesis of a variety of molecules having activity provides the possibility of a very wide range of uses . 2 : the establishment of a new method of a copper bromobenzoate catalytic substituted nitrile with an amidine or guanidine hydrochloride Synthesis aminoquinoline oxazoline type compounds . The catalyst is CuI (10mol%), ligand DMEDA ( 20 mol %) as the solvent , DMF, 80 ° C reaction . Cheap raw materials of the catalytic system under mild conditions , and the yield is higher . The synthesis product obtained for the synthesis of a variety of biologically and pharmaceutically active molecule may be provided.

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