Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes: [4 + 2] Cycloaddition Reaction of Amidines with 1,3,5-Triazines
β Scribed by Boger, Dale L.; Kochanny, Monica J.
- Book ID
- 115459521
- Publisher
- American Chemical Society
- Year
- 1994
- Tongue
- English
- Weight
- 727 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0022-3263
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Intermolecular cycloadditions between trialkyl 1,2,4-triazine-4,5,6-tricarboxyIatesand protected2-aminoimidazolegave IH-imidazo[4,5-c]pyridines (3-deazapurines)andthe rearranged3Hpyrido[3,2-d]pyrimid-4-ones (8-deazapteridines). No cycloadditions wereobservedwithimidazoleand2phenylimidazole.Q 1997Els
Imidazole and 2-phenylimidazoleundergo intramolecularcycloadditions with 1,2,4triazines tethered betweenan imidazolenitrogenand the triazinylC3 position with a trimethylene chainto producetetrahydro-l,5-naphthyridines followingloss of N2 and a nitrile.