書誌事項
- タイトル別名
-
- Studies on the Syntheses and Reaction of Nitrogen-Containing Heterocyclic Compounds Centered the Naphthyridines
- ナフチリジンルイ オ チュウシン ト シタ ガン チッソフクソカン カゴウブツ ノ ゴウセイ ト ハンノウ ノ ケンキュウ
この論文をさがす
抄録
1, X-Naphthyridines (X=5, 6, and 8) (1-3) were synthesized in a high yield by the Skraup reactions of 4-, 3-, and 2-aminopyridines with glycerol, in the presence of ferrous sulfate and boric acid. The improved syntheses were applied to the syntheses of 1, 5-, 1, 6-, and 1, 8-naphthyridines (4-28), pyridonaphthyridines (31, 32), benzonaphthyridines (38-42), naphthonaphthyridines (44, 48, 49, 59). New synthetic methods of naphtho [1, 2-b or 2, 1-b][1, 8]naphthyridine (62, 63), benzo[b][1, 8]naphthyridine (41) and benzo[g]quinoline (67) were developed and their compounds obtained conveniently. Reissert reaction of 1, 6-naphthyridine (2) using triethylbenzylammonium chloride (TEBA) produced Reissert compounds and ring-opened compounds. Reissert reaction of 1, 7-naphthyridine (29), 4, 7- (87), 4, 6-phenanthroline (38) gave the Reissert compounds, and the compounds (2, 38) gave their pseudo bases (79, 90). Reissert-type reactions of benzo[f]quinoline (68), and 1, 7-phenanthroline (105) with acyl chloride and phosphite, gave α-and γ-phosphonate, and 87 produced α, α'-(108a-c) and α, γ'-diphosphonates (109a-c). The structure of 108c-1 was determined to be trans-type by an X-ray analysis. Compounds 1-3, 29, and benzo[f or h]quinoline were treated with dimetyl sulfoxide in the presence of sodium hydride to give mainly methylated compounds at the position para to the ring-nitrogen. When benzo[f or h]quinoline N-oxide was treated with methylsulfinylmethyl carbanion in the usual procedure, a new reaction took place to produce phenanthrene in an excellent yield. The same reaction of 1, 10-, 1, 7-, or 4, 7-phenanthroline N-oxides (143-145) resulted in the liberation of the N-oxide group to form benzo [f or h]quinoline, but isoquinoline N-oxide afforded to benzazepine derivatives (161). Reaction of quinaldine with methylsulfinylmethyl carbanion gave novel tricyclic compound (121a). The oxidation of 41, 62, and 63 with peroxy acids afforded novel products such as seven-membered 1, 4-oxazepine derivatives.
収録刊行物
-
- 薬学雑誌
-
薬学雑誌 120 (2), 206-223, 2000
公益社団法人 日本薬学会
- Tweet
キーワード
詳細情報 詳細情報について
-
- CRID
- 1390282681132535168
-
- NII論文ID
- 110003648804
-
- NII書誌ID
- AN00284903
-
- ISSN
- 13475231
- 00316903
-
- NDL書誌ID
- 4971670
-
- データソース種別
-
- JaLC
- NDL
- Crossref
- CiNii Articles
-
- 抄録ライセンスフラグ
- 使用不可