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 journalArticle

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
Publication statusPublished - 1996 Apr
Externally publishedYes

Fingerprint

Pyrroles
Cycloaddition
Cycloaddition Reaction
Electrons
Alnus
Bearings (structural)
Hot Temperature

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

@article{59f21907ce014ad4b7e5139a0d436b4b,
title = "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",
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.",
keywords = "1H-pyrrole-2,3-dione, Claisen rearrangement, Dioxopyrroline, Hetero Diels Alder reaction, Normal Diels-Alder reaction",
author = "Yoshie Horiguchi and Takehiro Sano and Fumiyuki Kiuchi and Yoshisuke Tsuda",
year = "1996",
month = "4",
language = "English",
volume = "44",
pages = "681--689",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "4",

}

TY - JOUR

T1 - Dioxopyrrolines. LXI. Cycloaddition reaction of 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-dienes

T2 - Competitive occurrence of normal and hetero Diels-Alder reaction and Claisen rearrangement of the hetero Diels-Alder product

AU - Horiguchi, Yoshie

AU - Sano, Takehiro

AU - Kiuchi, Fumiyuki

AU - Tsuda, Yoshisuke

PY - 1996/4

Y1 - 1996/4

N2 - 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.

AB - 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.

KW - 1H-pyrrole-2,3-dione

KW - Claisen rearrangement

KW - Dioxopyrroline

KW - Hetero Diels Alder reaction

KW - Normal Diels-Alder reaction

UR - http://www.scopus.com/inward/record.url?scp=0029921534&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029921534&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0029921534

VL - 44

SP - 681

EP - 689

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 4

ER -