ORGN 18 |
| Synthesis of heterocyclic systems containing a linear array of heteroatoms (as in 3 and 4) presents a significant synthetic challenge. These systems are highly desirable building blocks which have applications in supramolecular polymers. We report a novel synthetic design strategy towards ADA and AADA linear arrays based on aza-anthracene and azanaphthacene systems. The synthetic strategy involves palladium catalyzed formation of the heterocyclic diarylamine 1 from commercially available pyridine precursors, and ring closure to 2 under acid conditions. Finally thermal electrocyclic ring opening, rearrangement and rearomatisation gives the 9H-1,8,9-triaza-anthracen-10-one 3; the tetraazanaphthacen-5-one 4 has been obtained by a similar strategy. The templates 3 and 4 provide access to novel AAA and AAAA systems.
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Heterocycles and Aromatics
8:00 AM-12:00 PM, Sunday, 13 March 2005 Convention Center -- Room 11A, Oral
Division of Organic Chemistry |
