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

作者：Nedolya Nina A^*; Tarasova Ol'ga A; Albanov Alexander I; Trofimov Boris A

来源：Tetrahedron Letters, 2010, 51(40): 5316-5318.

DOI：10.1016/j.tetlet.2010.07.179

• Allenes
• Alkynes
• 2-(Vinyloxy)ethyl isothiocyanate
• N-[2-(Vinyloxy)ethyl]
• and N-vinyl pyrroles
• Vinyl alcohol
• t-BuOK/DMSO
• C-O bond cleavage
• beta-Elimination

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.

• 出版日期2010-10-6