Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones

Erden I., Oezer G., Hoarau C., Cao W., Song J., Gaertner C., ...Daha Fazla

JOURNAL OF ORGANIC CHEMISTRY, cilt.73, sa.17, ss.6943-6945, 2008 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 17
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1021/jo801192z
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.6943-6945
  • Atatürk Üniversitesi Adresli: Hayır

Özet

5-Dialkylamino-4-pyrrolin-3-ones, available from cyclocondensation of amidines with dimethyl acetylenedicarboxylate (DMAD), undergo rapid singlet oxygenation to give highly functionalized ureas by way of a 1,2-dioxetane cleavage of the initially formed [2 + 2] cycloadducts. These latter compounds undergo cyclization to 2-oxazolidinones in MeOH. Catalytic hydrogenation of the ureas in EtOAc gives 2-oxazolinones. The DBU-DMAD adduct undergoes photooxygenation by an entirely different pathway to give a large ring heterocycle.