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 …

…, SM Lo, ZK Wan, GHC Woo, JK Snyder

Index: Lahue, Brian R.; Lo, Sie-Mun; Wan, Zhao-Kui; Woo, Grace H. C.; Snyder, John K. Journal of Organic Chemistry, 2004 , vol. 69, # 21 p. 7171 - 7182

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Citation Number: 53

Abstract

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 ...