Excellent acceleration of the Diels-Alder reaction by microwave irradiation for the synthesis of new fluorine-substituted ligands of NMDA receptor

Shigeki Sasaki, Nobuyasu Ishibashi, Tshuneo Kuwamura, Hiromi Sano, Masaki Matoba, Tohru Nisikawa, Minora Maeda

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A series of 6,11-ethanobenzo[b]quinolizinium derivatives was synthesized through the Diels-Alder reaction between azoniaanthracne and the corresponding 1,1-disubstituted olefin. After a systematic investigation for achieving rapid synthesis, it was found that the reaction is accelerated in polar media such as H2O and trifluoroethanol. In particular, excellent acceleration was effected by microwave irradiation. The new fluorine- substituted ligands thus obtained exhibited potential affinity toward NMDA receptors.

Original languageEnglish
Pages (from-to)2983-2986
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume8
Issue number21
DOIs
Publication statusPublished - Nov 1 1998

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Trifluoroethanol
Microwave irradiation
Fluorine
Cycloaddition Reaction
Alkenes
Microwaves
N-Methyl-D-Aspartate Receptors
Ligands
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Excellent acceleration of the Diels-Alder reaction by microwave irradiation for the synthesis of new fluorine-substituted ligands of NMDA receptor. / Sasaki, Shigeki; Ishibashi, Nobuyasu; Kuwamura, Tshuneo; Sano, Hiromi; Matoba, Masaki; Nisikawa, Tohru; Maeda, Minora.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 8, No. 21, 01.11.1998, p. 2983-2986.

Research output: Contribution to journalArticle

Sasaki, Shigeki ; Ishibashi, Nobuyasu ; Kuwamura, Tshuneo ; Sano, Hiromi ; Matoba, Masaki ; Nisikawa, Tohru ; Maeda, Minora. / Excellent acceleration of the Diels-Alder reaction by microwave irradiation for the synthesis of new fluorine-substituted ligands of NMDA receptor. In: Bioorganic and Medicinal Chemistry Letters. 1998 ; Vol. 8, No. 21. pp. 2983-2986.
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