ORGN 719 |
| As small nitrogen-containing cyclic compounds, 1,2,3,4-tetrahydro-2,5-naphthyridines have many desirable features. However, there are few known methods which are capable of preparing these scaffolds and while still allowing for ready diversification. The transition metal-catalyzed [2+2+2] cyclization of alkynes and nitriles has been recognized as a potential method for preparation of pyridine and related heterocycles. We have applied this chemistry to prepare diverse 1,2,3,4-tetrahydro-2,5-naphthyridines using microwave-promoted Co(I)-catalysis. In this presentation, we will review our studies towards the synthesis of 1,2,3,4-tetrahydro-2,5-naphthyridines using both intermolecular (Scheme 1) and intramolecular (Scheme 2) pathways including diversification involving various ring sizes, and introduction of chiral centers into cyclization precursors.
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Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, 1 September 2005 Washington DC Convention Center -- Ballroom B, Oral
Division of Organic Chemistry |
