A one-pot synthesis and mild cleavage of 2-[2- or 5-(alkylsulfanyl)pyrrol-1-yl]ethyl vinyl ethers by t-BuOK/DMSO: a novel and facile approach to N-vinylpyrroles |
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| Authors: | Nina A. Nedolya,Ol&rsquo ga A. Tarasova,Alexander I. Albanov,Boris A. Trofimov |
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| Affiliation: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation |
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| Abstract: | Substituted N-[2-(vinyloxy)ethyl]pyrroles, prepared in good yield through an allenic or acetylenic carbanion/isothiocyanate one-pot methodology from 2-(vinyloxy)ethyl isothiocyanate and allyloxyallene, methoxyallene, N,N-dimethyl-2-propyn-1-amine, and 3-methoxy-1-(methylsulfanyl)-1-propyne, are smoothly converted into the corresponding N-vinylpyrroles using t-BuOK/DMSO (room temperature). The reaction proceeds via elimination of vinyl alcohol from the N-[2-(vinyloxy)ethyl] substituent and represents a novel approach to N-vinylpyrroles. |
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| Keywords: | Allenes Alkynes 2-(Vinyloxy)ethyl isothiocyanate N-[2-(Vinyloxy)ethyl]- and N-vinyl pyrroles Vinyl alcohol t-BuOK/DMSO C-O bond cleavage β-Elimination |
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