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The Cs2CO3 -induced condensation of 2-(diazoacetyl)-2H-azirines with aromatic aldehydes does not result in the formation of an
azirinyl-substituted β-hydroxy-α-diazocarbonyl compound, but is accompanied by a tandem intramolecular cyclization involving the hydroxy group and the C=N bond of the azirine to form a bicyclic intermediate, a 4-diazo-2-oxa-7-azabicyclo[4.1.0]heptan-5-one derivative. The acid-catalyzed transformation of which leads to 2-aroyl-3-hydroxy-1H-pyrroles.
Original languageEnglish
Pages (from-to)897–904
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume22
DOIs
StatePublished - 9 Jun 2026

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  • Chemistry(all)

ID: 155510908