Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds

Michiharu Sugiura, Takeshi Usami, Yoshiki Hamada, Keiichiro Hatano, Yukihisa Kurono, Tamotsu Yashiro, Kimihiko Hirao, Kouichi Mogi

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Regiospecific nitration of quinoline and isoquinoline was achieved via the Reissert compounds by treatment with acetyl nitrate. Nitration of l-benzoyI-2-cyanoquinoline (3) afforded the 3-nitro derivative, which was converted to 3-nitroquinoline by hydrolysis with concentrated HC1. Meanwhile, 2-benzoyl-l-cyano-l,2-dihydroisoquinoline (4) was converted ultimately into 4-nitroisoquinoline-l-carboxylic acid (10) via 4-nitro-l-cyanoisoquinoline by the same procedure. A novel method for introducing a nitro group at the -position of a heterocyclic moiety has thus been developed. Crystal structure determinations and molecular orbital calculations of the Reissert compounds, are consistent with the regiospecific nitration.

Original languageEnglish
Pages (from-to)2262-2266
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume40
Issue number9
DOIs
Publication statusPublished - 1992
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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