Formation of cyclopropa[c]indole system in the Mn-mediated radical addition of cyclohexane-1,3-diones to N-substituted acrylamides

YILMAZ M., Birincioglu S., Inal A. U.

MENDELEEV COMMUNICATIONS, cilt.30, sa.6, ss.785-787, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 30 Sayı: 6
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.mencom.2020.11.032
  • Dergi Adı: MENDELEEV COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Communication Abstracts, Metadex
  • Sayfa Sayıları: ss.785-787
  • Anahtar Kelimeler: manganese(III) acetate, radical addition, dihydrofurans, benzofuran-2-carboxamides, cyclopropa[c]indoles, carboxamides, CERIUM(IV) AMMONIUM-NITRATE, FLUORINATED 1,3-DICARBONYL COMPOUNDS, ELECTRON-RICH ALKENES, MANGANESE(III) ACETATE, CYCLIZATION REACTIONS, EFFICIENT SYNTHESIS, DIASTEREOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, DIHYDROFURAN COMPOUNDS, OXIDATIVE CYCLIZATION
  • Kocaeli Üniversitesi Adresli: Evet

Özet

Manganese(III) acetate-mediated radical cyclization of N-substituted acrylamides with cyclohexane-1,3-diones gives 4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-2-carboxamides and unexpected tricyclic 1,1a,5,6-tetrahydro-2H-cyclopropa[c]indole-2,7(3H)-diones. The structure of one representative tricyclic compound was confirmed by X-ray analysis. The reaction mechanism was examined employing some structural analogues of the reactants.