Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 19, Pages 6644-6652Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1014933
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Funding
- National Natural Science Foundation of China [20832006]
- Ministry of Science and Technology of China [2009ZX09501-006]
- Beijing Municipal Commission of Education
- Scientific Research Foundation of Beijing Normal University [2009SC-1]
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The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields. This work not only provided the first example of the application of imidazo[1,5-a]pyridin-3-ylidenes in organic synthesis but also developed a straightforward approach to fully substituted furans that are not easily accessible by other methods.
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