A novel thermal rearrangement of allenic imidothioates. Formation of iminocyclobutenes |
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Authors: | Ol'ga A Tarasova Lambert Brandsma Alexander I Albanov |
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Institution: | a A. E. Favorsky Irkutsk Institute of Chemistry of the Russian Academy of Sciences, Siberian Branch, Favorsky Street 1, 664033 Irkutsk, Russia b Julianalaan 273, 3722 GN Bilthoven, The Netherlands |
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Abstract: | Allenic imidothioates, H2CCC(Ph)C(SMe)NR (R = Me, t-Bu, Ph) have been obtained in good yields by reaction of 1,3-dilithiated 1-(2-propynyl)benzene with isothiocyanates and successive addition of t-butyl alcohol and methyl iodide. Heating the imidothioates at ∼120 °C gave an iminocyclobutene as the only isolated product (if R = t-Bu), a ∼4:6 mixture of a 2,3-dihydropyridine and an iminocyclobutene (if R = Me) or a 3:1 mixture of a quinoline and an iminocyclobutene (if R = Ph). |
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Keywords: | 2-Propynylbenzene Isothiocyanates Allenyl imidothioates Cyclobutenes Dihydropyridines Quinolines Dilithiation Electrocyclisation |
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