Synthetic Protocols Mutually Applicable to 4-Oxoquinolines and 4-Oxo-1,8-naphthyridines: Synthesis of 1-Aryl-2-substituted and 1-Aryl-3-fluoro-4-oxoquinolines and 4-Oxo-1,8-naphthyridines

被引：7

作者：

Awasaguchi, Ken-ichiro ^{[1
]}

Hayashi, Hiromi ^{[1
]}

Kawai, Hyouei ^{[1
]}

Tominaga, Hiroko ^{[1
]}

Sato, Yuichiro ^{[1
]}

Hayashi, Kazuya ^{[1
]}

Todo, Yozo ^{[1
]}

机构：

[1] Toyama Chem Co Ltd, Res Labs, Discovery Res Dept, Toyama 9308508, Japan

来源：

SYNLETT | 2012年 / 03期

关键词：

antiviral agents; heterocycles; HIV; 4-oxoquinoline; 4-oxo-1,8-naphthyridine; fluorocyclization; CATALYZED AMIDATION; ANTITUMOR AGENTS; 4-QUINOLONES; CYCLIZATION; INHIBITORS; QUINOLONE; ACIDS;

D O I：

10.1055/s-0031-1290079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have achieved the synthesis of 1-aryl-2-substituted 4-oxoquinoline and 4-oxo-1,8-naphthyridine derivatives, which cannot be synthesized by known methods, via two useful synthons, 2-formyl-4-oxoquinoline and 2-methylsulfonyl-4-oxo-1,8-naphthyridine. We also succeeded in the synthesis of 1-aryl-3-fluoro-4-oxoquinoline by fluorocyclization of N-arylenaminone with Selectfluor (R) and potassium carbonate in DMF in a one-pot procedure. To the best of our knowledge, this is the first synthesis of 3-fluoro-4-oxoquinoline derivatives. We confirmed that these protocols were mutually applicable to the synthesis of 4-oxoquinoline and 4-oxo-1,8-naphthyridine derivatives.

引用

页码：448 / 452

页数：5

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