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Sulfur ylides. 11. Selected chemical transformations of 1-methylthio-3,4-dihydropyrido[2,1-a]isoindole-2,6-dione

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Abstract

The reaction of 1-methylthio-3,4-dihydropyrido[2,1-a]isoindole-2,6-dione (2) with NaBH4 led to reduction of the keto group to the hydroxy group. The reaction with the use of LiAlH4 resulted in complete reduction of the carboximide group, reduction of the keto group to the hydroxy function, and reduction of the double bond accompanied by desulfurization. The reaction of indolizidinedione 2 with Zn afforded a reductive desulfurization product. The reactions of 2 with hydrazine hydrate, hydroxylamine, and formamide proceeded according to a mechanism typical of the keto group to give hydrazone, oxime, and the formyl derivative, respectively. Oxidation of the thiomethyl group of the starting compound with ButOOH gave rise to sulfone or sulfoxide depending on the amount of the oxidizing agent used.

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Refenrences

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Authors and Affiliations

  1. Ufa Research Center of the Russian Academy of Sciences, Institute of Biology, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    S. N. Lakeev & I. O. Maydanova

  2. Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    I. Z. Myllagalin, F. Z. Galin, G. F. Vafina & G. A. Tolstikov

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  1. S. N. Lakeev
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  2. I. Z. Myllagalin
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  3. F. Z. Galin
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  4. I. O. Maydanova
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  5. G. F. Vafina
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  6. G. A. Tolstikov
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Lakeev, S.N., Myllagalin, I.Z., Galin, F.Z. et al. Sulfur ylides. 11. Selected chemical transformations of 1-methylthio-3,4-dihydropyrido[2,1-a]isoindole-2,6-dione. Russian Chemical Bulletin 51, 1035–1038 (2002). https://doi.org/10.1023/A:1019626005246

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  • DOI: https://doi.org/10.1023/A:1019626005246

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