Regiospecific Nitration of Quinoline and isoquinoline through the Reissert Compounds
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- 杉浦 道治
- Faculty of Pharmacy, Meijo University
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- 畑野 研一郎
- Faculty of Pharmaceutical Sciences, Nagoya City University
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- 平尾 公彦
- Department of Chemistry, Faculty of General Education
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- 茂木 孝一
- Department of Chemistry, Faculty of Science
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- 黒野 幸久
- Faculty of Pharmaceutical Sciences, Nagoya City University
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- 八代 有
- Faculty of Pharmaceutical Sciences, Nagoya City University
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- 宇佐見 健
- Faculty of Pharmacy, Meijo University
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- 濱田 喜樹
- Faculty of Pharmacy, Meijo University
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抄録
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.
収録刊行物
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- Chemical & pharmaceutical bulletin
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Chemical & pharmaceutical bulletin 40 (9), 2262-2266, 1992-09-25
公益社団法人日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1571698602302207104
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- NII論文ID
- 110003630202
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- NII書誌ID
- AA00602100
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- ISSN
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- CiNii Articles