Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions. 4. Intermolecular reactions with 1,2,4-triazines |
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Authors: | Lahue Brian R Wan Zhao-Kui Snyder John K |
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Affiliation: | Department of Chemistry, Boston University, 590 Commonwealth Avenue, Massachusetts 02215, USA. |
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Abstract: | Intermolecular inverse electron demand cycloadditions of 2-substituted imidazoles with various 1,2,4-triazines produced both imidazo[4,5-c]pyridines (3-deazapurines) and pyrido[3,2-d]pyrimid-4-ones (8-deazapteridines). The product distribution was controlled by reactant substituents and influenced by reaction temperature. A regioselective method for the preparation of 6-unsubstituted 1,2,4-triazines was also developed. By using this route to 8-deazapteridines, a new 8-deazafolate analogue was prepared. |
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