Regiospecific Nitration of Quinoline and isoquinoline through the Reissert Compounds

• SUGIURA Michiharu

  Faculty of Pharmacy, Meijo University

• HATNO Keiichiro

  Faculty of Pharmaceutical Sciences, Nagoya City University

• HIRAO Kimihiko

  Department of Chemistry, Faculty of General Education

• MOGI Kouichi

  Department of Chemistry, Faculty of Science

• KURONO Yukihisa

  Faculty of Pharmaceutical Sciences, Nagoya City University

• YASHIRO Tamotsu

  Faculty of Pharmaceutical Sciences, Nagoya City University

• USAMI Takeshi

  Faculty of Pharmacy, Meijo University

• HAMADA Yoshiki

  Faculty of Pharmacy, Meijo University

Abstract

Regiospecific nitration of quinoline and isoquinoline was achieved via the Reissret compounds by treatment with acetyl nitrate. Nitration of 1-benzoyl-2-cyanoquinoline (3) afforded the 3-nitro derivative, which was converted to 3-nitroquinoline by hydrolysis with concentrated HCl. Meanwhile, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline (4) was converted ultimately into 4-nitroisoquinoline-1-carboxylic acid (10) via 4-nitro-1-cyanoisoquinoline by the same procedure. A novel method for introducing a nitro group at the β-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.

Journal

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 40 (9), 2262-2266, 1992-09-25

  The Pharmaceutical Society of Japan

Keywords

• Reissert compound
• pseudo-base
• quinoline
• isoquinoline
• regiospecific nitration
• heterocyle nitration
• X-ray crystal structure
• molecular orbital calculation
• COSY
• NOE

Details

• CRID: 1571698602302207104
• NII Article ID: 110003630202
• NII Book ID: AA00602100
• ISSN: 00092363
• Text Lang: en
• Data Source:
  • CiNii Articles