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 |
| |
| Authors: | Nina A Nedolya Ol’ga A Tarasova Alexander I Albanov Boris A Trofimov |
| |
| Institution: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation |
| |
| 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. |
| |
| 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 |
| 本文献已被 ScienceDirect 等数据库收录！ |
