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KMID : 1059520130570030361
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Journal of the Korean Chemical Society
2013 Volume.57 No. 3 p.361 ~ p.364
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Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP
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Sajith Ayyiliath M.
Muralidharan Arayambath
Karuvalam Ranjith P.
Haridas Karickal R.
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Abstract
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A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[ 4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.
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KEYWORD
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Buchwald coupling, Imidazopyridine, Suzuki coupling, Heterocyclic amines
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