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Cyclization Reactions of 2-Isothiocyanatophenyl Ketones Giving 4-Hydroxyquinoline-2(1H)-thiones and 4-Alkylidene-1,4-dihydro-3,1-benzoxazine-2-thiones
2010
Heterocycles
2-Isothiocyanatophenyl methyl ketones, generated in situ by treatment of 2-isocyanophenyl methyl ketones with sulfur in the presence of a catalytic amount of selenium and excess triethylamine, underwent electrocyclic reaction (ECR) via their enolate forms to give 4-hydroxyquinoline-2(1H)-thiones. The reaction products from ethyl 2-isothiocyanatophenyl ketones generated in situ from the corresponding isocyanides under similar conditions proved to be the ECR products,
doi:10.3987/com-10-11991
fatcat:i7v7yjyitvfarpw72dmgqaldbq