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Synthesis of Substituted Imidazo[1,5-a]pyrazines via Mono-, Di-, and Directed Remote Metalation Strategies
- Source :
- Organic Letters. 11:5118-5121
- Publication Year :
- 2009
- Publisher :
- American Chemical Society (ACS), 2009.
-
Abstract
- Imidazo[1,5-a]pyrazines 1 undergo regioselective C3-metalation and C5/C3-dimetalation to afford a range of functionalized derivatives 2a-2g (Table 1 ), and 4a-4d (Table 2 ). Under similar conditions, the C3-methyl derivatives 2a and 5 undergo surprising regioselective C5-deprotonation to afford, after electrophile quench, products 4b and 6a-6p (Table 3 ), results that are rationalized by quantum mechanical calculations. Benzamide 7b, obtained from such metalation chemistry followed by Suzuki cross coupling, undergoes directed remote metalation-cyclization to afford 8, representing the hitherto unknown triazadibenzo[cd,f]azulen-7(6H)-one tricyclic ring system.
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 11
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....7990c1ac5792c60142b9925fc01055b3