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Intramolecular Inverse-Electron-Demand Diels−Alder Reactions of Imidazoles with 1,2,4-Triazines: A New Route to 1,2,3,4-Tetrahydro-1,5-naphthyridines and Related Heterocycles

2004; American Chemical Society; Volume: 69; Issue: 21 Linguagem: Inglês

10.1021/jo040193z

1520-6904

Brian R. Lahue, Sie‐Mun Lo, Zhao‐Kui Wan, Grace H. C. Woo, John K. Snyder,

Chemical Reaction Mechanisms

The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.