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Reaction of sulfene with heterocyclic N,N-disubstituted α-aminomethyleneketones. IX. Synthesis of 1,2-oxathiino[6,5-e]indole derivatives
Authors:Luisa Mosti  Pietro Schenone  Giulia Menozzi  Sergio Cafaggi
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-NR2 = dimethylamino) with DDQ in refluxing benzene gave in low yield 7-methyl-7H-1,2-oxathiino-[6,5-e]indole 2,2-dioxide, whereas the same reaction of IVe (4-NR2 = morpholinyl) with excess DDQ afforded in low yield 7-methyl-4-morpholinyl-7H-1,2-oxathiino[6,5-e]indole 2,2-dioxide.
Keywords:
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