Dienophilicity of Imidazole in Inverse Electron Demand Diels-Alder Reactions; Intermolecular Reactions with 1,2,4-Triazines.
✍ Scribed by Zhaokui Wan; John K Snyder
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 582 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 1997Elsevier Science Ltd.
📜 SIMILAR VOLUMES
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.
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The Diels-Alder reaction of 4-aryl-pyrones with electron-rich dienophiles afforded substituted biaryl derivatives in most cases. At the minimal temperatures necessary for a measurable conversion of the starting pyrones, the bicyclic lactones, the primary products of the condensation, underwent cyclo