Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 9167-9174Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01714
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Funding
- Ministry of Education ARC [R-143-000-603-112, R-143-000-550-112]
- NUS
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A versatile protocol for the synthesis of disubstituted 3-phenylimidazo[1,2-a]pyridines by coupling 2-aminopyridine with phenylacetophenones, phenylacetones, or beta-tetralone has been developed. Isolated yields of up to 97% were obtained at 80 degrees C within 5 h. The 2-aminopyridine/CBrCl3 system acts as an alpha-bromination shuttle by transferring Br from CBrCl3 to the alpha-carbon of the carbonyl moiety. This triggers a series of steps with double C-N/C-N bond formation to the final product. The distinct advantages of this protocol include the use of commercially available inexpensive substrates, simplicity of a metal-free one-pot synthesis, and ease of scale-up to multigram quantities.
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