Synthesis of New Crown Ethers Containing Appended Pyridine, 10-hydroxybenzoquinoline, 8-hydroxyquinoline and 2-amino-1-hydroxybiphenyl Sidearms |
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Authors: | Hua-Can Song Jerald S Bradshaw Yi-Wen Chen Guo-Ping Xue Wei-Ming Li Krzysztof E Krakowiak |
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Institution: | 1. Department of Chemistry , Zhongshan University , Guangzhou , 510275 , People's Republic of China;2. Department of Chemistry and Biochemistry , Brigham Young University , Provo , UT , 84602 , USA;3. IBC Advanced Technologies Inc. , 856 East Utah Valley Drive, American Fork , UT , 84003 , USA |
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Abstract: | Twelve crown ethers containing one or two arms were synthesized. Two methods were used to attach arms to the azacrown ethers. Ligands 4 - 12 were prepared by a nucleophilic substitution of secondary macrocyclic amine functions on RX ( X=bromide or tosylate groups). Ligands 13 - 15 were obtained via a Mannich reaction of secondary macrocyclic amines with 5-chloro-8-hydroxyquinoline or a substituted-phenol. Diaza-18-crown-6 was treated with 2-bromomethyl-9-methyl-1,10-phenanthroline at the same conditions in which 4 - 8 and 10 - 12 were prepared. In this case, the main product was the diazacrown ether containing one arm. Twelve new aza-crown ethers bearing aromatic and aliphatic side arms were prepared by nucleophilic substitution by secondary macrocyclic amine functions on halide or tosylates or via a Mannich reaction of the macrocyclic secondary amines with phenolic compounds. R=derivatives of pyridine, 8-hydroxyquiniline, and 1-hydroxybiphenyl. Crown ether include aza-15-crown-5 diaza-18-crown-6 diazatrithia-15 (and 16)-crown-6 and diaza-21-crown-7 |
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Keywords: | Lariat Ethers Syntheses Substitution And Mannich Reaction |
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