Reaction of sulfene with heterocyclic N, N??disubstituted α??aminomethyleneketones. IX. Synthesis of 1, 2??oxathiino [6, 5??e] indole derivatives

…, P Schenone, G Menozzi, S Cafaggi

Index: Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia; Cafaggi, Sergio Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 1031 - 1034

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Abstract

Abstract The polar 1, 4-cycloaddition of sulfene to N, N-disubstituted 5-aminomethylene-1, 5, 6, 7-tetrahydro-1-methylindol-4-ones occurred only in the case of aliphatic N-substitution to give, generally in good yield, 4-dialkylamino-3, 4, 5, 6-tetrahydro-7-methyl-7H-1, 2-oxathiino [6, 5-e] indole 2, 2-dioxides IV. Full aromatization of IVa (4-NR 2= dimethylamino) with DDQ in refluxing benzene gave in low yield 7-methyl-7H-1, 2-oxathiino-[6, 5-e] indole 2, 2- ...