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Synthesis 2009(15): 2531-2534  
DOI: 10.1055/s-0029-1217397
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Gas-Phase Synthesis of N-Unsubstituted 3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones

Lawrence Hilla, Gordon A. Hunterb, 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;
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Publication History

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

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Abstract

Flash vacuum pyrolysis (FVP) at 600 ˚C of methylaminomethylene derivatives of Meldrum’s acid bearing electron-withdrawing substituents on the methyl group, provides N-unsubstituted 3-hydroxypyrroles and/or 1H-pyrrol-3(2H)-ones in high yield.

Key words

gas-phase reactions - pericyclic reactions - heterocycles - pyrroles - regioselectivity

    References

  • Reviews:
  • 1a McNab H. Monahan LC. Pyrroles   Vol. 2:  Jones RA. Wiley; New York: 1992.  p.525 
    Search in Google Scholar
  • 1b Gaber AM. McNab H. Synthesis  2001,  2059 
  • 2 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1  1988,  863 
    Crossref
  • 3 Blake AJ. Hunter GA. McNab H. J. Chem. Soc., Chem. Commun.  1990,  734 
    Crossref
  • 4 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1  1988,  869 
    Crossref
  • 5 George L. Wong MW. Wentrup C. Org. Biomol. Chem.  2007,  5:  1437 
    CrossrefSearch in Google Scholar
  • 6a Gordon HJ. Martin JC. McNab H. J. Chem. Soc., Perkin Trans. 1  1984,  2129 
  • 6b Briehl H. Lukosch A. Wentrup C. J. Org. Chem.  1984,  49:  2772 
    Search in Google Scholar
  • 7 McNab H. Withell K. ARKIVOC  2000,  (v):  806 
    Search in Google Scholar
  • 8 Gaber AM. Hunter GA. McNab H. J. Chem. Soc., Perkin Trans. 1  2002,  548 
    Crossref
  • 9a Momose T. Tanaka T. Yokota T. Nagamoto N. Yamada K. Chem. Pharm. Bull.  1978,  26:  2224 
    Search in Google Scholar
  • 9b Zvilichovsky G. Gurvich V. Tetrahedron  1995,  51:  5479 
    Search in Google Scholar
  • 10 Frisch MJ. Trucks GW. Schlegel HB. Scuseria GE. Robb MA. Cheeseman JR. Montgomery JA. Vreven T. Kudin KN. Burant JC. Millam JM. Iyengar SS. Tomasi J. Barone V. Mennucci B. Cossi M. Scalmani G. Rega N. Petersson GA. Nakatsuji H. Hada M. Ehara M. Toyota K. Fukuda R. Hasegawa J. Ishida M. Nakajima T. Honda Y. Kitao O. Nakai H. Klene M. Li X. Knox JE. Hratchian HP. Cross JB. Bakken V. Adamo C. Jaramillo J. Gomperts R. Stratmann RE. Yazyev O. Austin AJ. Cammi R. Pomelli C. Ochterski JW. Ayala PY. Morokuma K. Voth GA. Salvador P. Dannenberg JJ. Zakrzewski VG. Dapprich S. Daniels AD. Strain MC. Farkas O. Malick DK. Rabuck AD. Raghavachari K. Foresman JB. Ortiz JV. Cui Q. Baboul AG. Clifford S. Cioslowski J. Stefanov BB. Liu G. Liashenko A. Piskorz P. Komaromi I. Martin RL. Fox DJ. Keith T. Al-Laham MA. Peng CY. Nanayakkara A. Challacombe M. Gill PMW. Johnson B. Chen W. Wong MW. Gonzalez C. Pople JA. Gaussian03   Gaussian Inc.; Wallingford CT: 2004. 
  • 11 Hill L. Imam SH. McNab H. O’Neill WJ. Synthesis  2009,  2535