Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
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)
![](https://www.thieme-connect.de/media/synthesis/200915/lookinside/thumbnails/10.1055-s-0029-1217422-1.jpg)
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
- 1 For example:
Zotti G.Zecchin S.Schiavon G.Groenendaal LB. Chem. Mater. 2000, 12: 2996 -
2a
Capon B.Kwok FC. Tetrahedron Lett. 1986, 27: 3275 -
2b
Capon B.Kwok FC. J. Am. Chem. Soc. 1989, 111: 5346 - 3
Hill L.Imam SH.McNab H.O’Neill WJ. Synthesis 2009, 2531 - 4 Review:
Gaber AM.McNab H. Synthesis 2001, 2059 - 5
McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1988, 863 - 6
De Puy CH.King RW. Chem. Rev. 1960, 60: 431 - 7 Review:
McNab H.Monahan LC. In Pyrroles Vol. 2:Jones RA. Wiley; New York: 1992. p.525 - 8
McNab H.Withell K. ARKIVOC 2000, (v): 806 -
9a
McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 2 1991, 1999 -
9b
McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 2 1988, 1459 - 10
Blake AJ.McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 2 1988, 1455 - 11 Cf.:
Blake AJ.McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 2 1988, 1463 - 12 Cf.:
Blake AJ.McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1991, 701 - 13 Cf.:
Derbyshire PA.Hunter GA.McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1993, 2017 - 14
Kawasaki T.Tang C.-Y.Nakanishi H.Hirai S.Ohshita T.Tanizawa M.Himori M.Satoh H.Sakamoto M.Miura K.Nakano F. J. Chem. Soc., Perkin Trans. 1 1999, 327 - 15
Hunter GA. Ph. D. Thesis The University of Edinburgh; Scotland: 1990.