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3688355 
Journal Article 
3-Hydroxy-1H-pyrrole 
Hill, L; Imam, SH; Mcnab, H; O'Neill, WJ 
2009 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
Synthesis-Stuttgart 
2009 
15 
2535-2538 
WOS:000269084500010 
Abstract: Flash vacuum pyrolysis (FVP) of tert-butyl {[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}acetate at 600 degrees 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. ds: Chemistry cument Delivery No.: 484XV e field[29]: 1,4-Dioxane 
gas-phase reactions; heterocycles; pyrroles; electrophilic aromatic substitutions; tautomerism