Dioxopyrrolines. LXI. Cycloaddition reaction of 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-dienes: Competitive occurrence of normal and hetero Diels-Alder reaction and Claisen rearrangement of the hetero Diels-Alder product

Yoshie Horiguchi, Takehiro Sano, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Thermal cycloaddition reaction of 4-benzoyl-5-ethoxycarbonyl-1H-pyrrole-2,3-dione (dioxopyrroline) 1 with 1,3-dienes caused two types of Diels-Alder (D-A) reaction in a competitive manner. One is the hetero D-A reaction in which dioxopyrroline acts as an electron-deficient diene and the 1,3-diene acts as an electron-rich dienophile. The other is the normal D-A reaction in which dioxopyrroline acts as an electron-deficient dienophile. The 1,3-dienes bearing electron-rich substituents undergo the D-A reaction via the normal pathway, while the 1,3-dienes which do not bear an electron-donating group predominantly undergo the hetero D-A reaction. When the normal D-A pathway is sterically hindered, the hetero D-A pathway occurs exclusively.

Original languageEnglish
Pages (from-to)681-689
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume44
Issue number4
DOIs
Publication statusPublished - 1996 Apr
Externally publishedYes

Keywords

  • 1H-pyrrole-2,3-dione
  • Claisen rearrangement
  • Dioxopyrroline
  • Hetero Diels Alder reaction
  • Normal Diels-Alder reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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