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Synthesis 1997; 1997(3): 271-272
DOI: 10.1055/s-1997-1192
short paper
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Methyl 2H-Azirine-3-carboxylates as Dienophiles: Synthesis of Methyl 1-Azabicyclo[4.1.0]-hept-3-ene-6-carboxylates

Pamila Bhullar1 , Thomas L. Gilchrist2 , Peter Maddocks1
  • 1Chemical Development Laboratories, Glaxo Wellcome, Temple Hill, Dartfort, Kent DA1 5AH, UK
  • 2Chemistry Department, University of Liverpool, Liverpool L69 3BX, UK, Fax +44(151)7943588; E-mail tlg57@liv.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Methyl 2-aryl-2H-azirine-3-carboxylates are good dienophiles. They react with cyclopentadiene, cyclohexa-1,3-diene and 2,3-dimethylbuta-1,3-diene at or below 50°C to give products of [4+2]-cycloaddition to the carbon-nitrogen double bond. The cycloadditions are endo selective and the dienophiles approach from the less hindered face of the azirines.

2H-azirines - imines - Diels-Alder reaction