First example of the synthesis of N-vinylpyrrole from methoxyallene and methoxyethyl isothiocyanate: unprecedented elimination of methanol from a [beta]-substituted methyl ethyl ether

First example of the synthesis of N-vinylpyrrole from methoxyallene and methoxyethyl isothiocyanate: unprecedented elimination of methanol from a [beta]-substituted methyl ethyl ether

Using as example 3-methoxy-1-(2-methoxyethyl)-2-methylsulfanylpyrrole, obtained in one preparative stage from [alpha]-lithiated methoxyallene and 2-methoxyethyl isothiocyanate, a facile cleavage of a C-O bond in the N-(2-methoxyethyl) substituent by the t-BuOK-DMSO system has been discovered, openin...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2010-05, Vol.46 (1), p.61
Hauptverfasser: Nedolya, N.A, Tarasova, O.A, Albanov, A.I, Klyba, L.V, Trofimov, B.A
Format: Artikel
Sprache:eng
Schlagworte:
Methanol
Organic compounds
Synthesis
Thiophene
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Zusammenfassung:Using as example 3-methoxy-1-(2-methoxyethyl)-2-methylsulfanylpyrrole, obtained in one preparative stage from [alpha]-lithiated methoxyallene and 2-methoxyethyl isothiocyanate, a facile cleavage of a C-O bond in the N-(2-methoxyethyl) substituent by the t-BuOK-DMSO system has been discovered, opening access to a new class of N-vinylpyrroles (through [beta]-elimination of methanol). Keywords: N-vinylpyrrole, methoxyallene, N-(2-methoxyethyl)pyrrole, 2- methoxyethyl isothiocyanate, t-BuOK-DMSO system, synthesis, [beta]-elimination.
ISSN:0009-3122