198549-10-9Relevant articles and documents
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
Lahue, Brian R.,Lo, Sie-Mun,Wan, Zhao-Kui,Woo, Grace H. C.,Snyder, John K.
, p. 7171 - 7182 (2007/10/03)
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.
Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions; intramolecular reactions with 1,2,4-triazines
Neipp, Christopher E.,Ranslow, Peter B.,Wan, Zhaokui,Snyder, John K.
, p. 7499 - 7502 (2007/10/03)
Imidazole and 2-phenylimidazole undergo intramolecular cycloadditions with 1,2,4-triazines tethered between an imidazole nitrogen and the triazinyl C3 position with a trimethylene chain to produce tetrahydro-1,5-naphthyridines following loss of N2/s