Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds

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

Research output: Contribution to journalArticle

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 - Jan 1 1992

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Nitration
Nitroquinolines
Carboxylic Acids
Molecular Structure
Nitrates
Orbital calculations
Hydrolysis
Molecular orbitals
Crystal structure
Derivatives
quinoline
isoquinoline
G 1617

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds. / Sugiura, Michiharu; Usami, Takeshi; Hamada, Yoshiki; Hatano, Keiichiro; Kurono, Yukihisa; Yashiro, Tamotsu; Hirao, Kimihiko; Mogi, Koichi.

In: Chemical and Pharmaceutical Bulletin, Vol. 40, No. 9, 01.01.1992, p. 2262-2266.

Research output: Contribution to journalArticle

Sugiura, M, Usami, T, Hamada, Y, Hatano, K, Kurono, Y, Yashiro, T, Hirao, K & Mogi, K 1992, 'Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds', Chemical and Pharmaceutical Bulletin, vol. 40, no. 9, pp. 2262-2266. https://doi.org/10.1248/cpb.40.2262
Sugiura, Michiharu ; Usami, Takeshi ; Hamada, Yoshiki ; Hatano, Keiichiro ; Kurono, Yukihisa ; Yashiro, Tamotsu ; Hirao, Kimihiko ; Mogi, Koichi. / Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds. In: Chemical and Pharmaceutical Bulletin. 1992 ; Vol. 40, No. 9. pp. 2262-2266.
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