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Synthesis 2009(15): 2535-2538
DOI: 10.1055/s-0029-1217422
DOI: 10.1055/s-0029-1217422
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
3-Hydroxy-1H-pyrrole
Further Information
Received
8 April 2009
Publication Date:
23 June 2009 (online)
Publication History
Publication Date:
23 June 2009 (online)
Abstract
Flash vacuum pyrolysis (FVP) of tert-butyl {[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}acetate at 600 ˚C gives the unstable 3-hydroxy-1H-pyrrole in ca. 55% yield as the only significant product. It exists as the enol tautomer in dimethyl sulfoxide solution, and predominantly as the keto tautomer in water. 3-Hydroxy-1H-pyrrole reacts readily with mild electrophiles, exclusively at the 2-position. FVP of the product obtained from one such reaction with methoxymethylene-substituted Meldrum’s acid gives pyrano[3,2-b]pyrrol-5(1H)-one in 77% yield.
Key words
gas-phase reactions - heterocycles - pyrroles - electrophilic aromatic substitutions - tautomerism
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