Journal
ORGANIC LETTERS
Volume 15, Issue 9, Pages 2290-2293Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400870b
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- FRQNT Centre in Green Chemistry and Catalysis
- Universite de Montreal
- NSERC
- FRQNT
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Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira cross-coupling and direct arylation reactions. A tertiary amide was compatible as a substrate leading to the synthesis of an imidazo[1,5-a]pyridinium triflate.
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