Competitive intramolecular Diels-Alder reaction and intramolecular coplanar cycloamination of 3-(3-butynylthio)-1, 2, 4-triazin-5-ones

…, JL Pont, D Van Engen, JC Warner

Index: Taylor, Edward C.; Pont, Joseph L.; Engen, Donna van; Warner, John C. Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 5093 - 5097

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Citation Number: 6

Abstract

3-(3-Butynylthio)-l, 2, 4-triazin-5-ones 2 participate in competitive intramolecular Diels-Alder (IDA) and intramolecular coplanar cycloamination (ICC) processes to provide 2, 3- dihydrothieno [2, 3-b] pyridin-6 (7W-ones 3 and 8-methylene-7, 8-dihydro-3H, GH-[1, 3] thiazino [3, 2-~]-1, 2, 4-triazin-3-ones 4, respectively. In relatively inert aromatic solvent systems, the ratio of IDA to ICC products is markedly dependent on the electronic ...