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Synthesis 2009(15): 2535-2538  
DOI: 10.1055/s-0029-1217422
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-Hydroxy-1H-pyrrole

Lawrence Hilla, S. Haider Imama, Hamish McNab*b, William J. O’Neillb
a Durham Organics Ltd., Units 12-14, Langley Moor Industrial Estate, Langley Moor, Durham, DH7 8JE, UK
b School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;
Further Information

Publication History

Received 8 April 2009
Publication Date:
23 June 2009 (online)

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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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