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 language | English |
|---|---|
| Pages (from-to) | 2262-2266 |
| Number of pages | 5 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 40 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - Jan 1 1992 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Drug Discovery
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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 journal › Article
}
TY - JOUR
T1 - Regiospecific Nitration of Quinoline and Isoquinoline through the Reissert Compounds
AU - Sugiura, Michiharu
AU - Usami, Takeshi
AU - Hamada, Yoshiki
AU - Hatano, Keiichiro
AU - Kurono, Yukihisa
AU - Yashiro, Tamotsu
AU - Hirao, Kimihiko
AU - Mogi, Koichi
PY - 1992/1/1
Y1 - 1992/1/1
N2 - 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.
AB - 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.
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U2 - 10.1248/cpb.40.2262
DO - 10.1248/cpb.40.2262
M3 - Article
VL - 40
SP - 2262
EP - 2266
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 9
ER -