Intramolecular Diels-Alder reactions of 1, 2, 4-triazines. Synthesis of 2, 3-cyclopentenopyridines and 5, 6, 7, 8-tetrahydroquinolines

EC Taylor, JE Macor, LG French

Index: Taylor, Edward C.; Macor, John E.; French, Larry G. Journal of Organic Chemistry, 1991 , vol. 56, # 5 p. 1807 - 1812

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Citation Number: 47

Abstract

Intramolecular inverse-electron-demand Diels-Alder reactions of 1, 2, 4-triazines constitute a versatile method for the preparation of a variety of functionalized, fused heterocycles. 2 Application of this method to the preparation of fused pyridines requires an alkyne or alkene (or their equivalents) as the dienophilic component which, when tethered to C-3 of the 1, 2, 4- triazine, leads to fused [2, 3-b] pyridines following cycloaddition and nitrogen extrusion. ...