Development of a Novel Approach to Formation of a Pyrrole Ring: Synthesis of 2,3,5-Substituted 1-[2-(Vinyloxy)ethyl]pyrroles |
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| Authors: | L. Brandsma N. A. Nedolya S. V. Tolmachev |
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| Affiliation: | (1) Utrecht University, Utrecht, 3584 CH, The Netherlands;(2) Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia |
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| Abstract: | Reaction of 2-(vinyloxy)ethylisothiocyanate with unsaturated carbanions generated in situ from propargyl ethers and amines when treated with superbases, after S-alkylation and cyclization of the adducts in the presence of CuBr, leads to the previously unknown 2,3,5-substituted 1-[2-(vinyloxy)ethyl]pyrroles. |
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| Keywords: | 2-alkynes 2,3-butadiene imidothioates 2-(vinyloxy)ethylisothiocyanate 1-[2-(vinyloxy)ethyl]pyrroles superbases deprotonation catalysis cyclization |
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