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タイトルReactions of 7h-naphth[3,2,1-cd]azulen-7-ones
作成者Abe, Noritaka
Fujii, Hiroyuki
Takase, Kahei
Morita, Tadayoshi
作成者ヨミアベ, ノリタカ
フジイ, ヒロユキ
タカセ, カヘイ
モリタ, タダヨシ
作成者別表記阿部, 憲孝
藤井, 寛之
作成者所属山口大学大学院医学系研究科(理学)
内容記述(抄録等)6-Chloro-7H-naphth[3,2,1-cd]azulen-7-ones 9a and 10a easily react with some nucleophiles (sodium methoxide, potassium hydrosulfide, and amines) to give the corresponding 6-substituted products. Halogenation of 7H-naphth[3,2,1-cd]azulen-7-ones with N-halosuccinimides occurs at the C-5 position. Grignard reagents add to 7H-naphth[3,2,1-cd]azulen-7-ones at the seven-membered ring and a subsequent dehydrogenation gives 2-, 3- and 4-substituted products; reactive tendency of the positions of 7H-naphth[3,2,1-cd]azulen-7-one toward the reagents was 6 》 3 > 4 > 2, whereas the steric hindrance was (6 >) 4 > 3 > 2. Condensation of 7H-naphth[3,2,1-cd]azulen-7-ones with active methylene compounds in boiling acetic anhydride occurs at the carbonyl group and gives the corresponding 7-methylene-7H-naphth[3,2,1-cd]azulene derivatives. 6-Hydroxy-7H-naphth[3,2,1-cd]azulen-7-one 7 is obtained by the hydrolysis of 6-methoxy-7H-naphth[3,2,1-cd]azulen-7-one 9b with hydrobromic acid, in almost quantitative yield. Compound 7 exists in a tautomeric mixture with 7-hydroxy-6H-naphth[3,2,1-cd]azulen-6-one 8. Methylation of 7 with diazomethane gives 9b and 7-methoxy-6H-naphth[3,2,1-cd]azulen-6-one 18a in 75% and 25% yield, respectively. Chlorination of 7 with thionyl dichloride also gives a pair of isomers, 5,6-dichloro-7H-naphth[3,2,1-cd]azulen-7-one 11b and 5,7-dichloro-6H-naphth[3,2,1-cd]azulen-6-one 18b. A tautomerism between 6-(substituted methyl)-7H-naphth[3,2,1-cd]azulen-7-ones and 7-hydroxy-6H-naphth[3,2,1-cd]azulen-6-ylidenemethylene derivative is also studied.
本文言語eng
資料タイプtext
出版者Royal Society of Chemistry
NII資料タイプ学術雑誌論文
査読の有無査読あり
ISSN1472-7781
NCIDAA11413675
掲載誌名Perkin. 1 : an international journal of organic and bio-organic chemistry
2001
12
開始ページ1359
終了ページ1365
発行日2001
DOIinfo:doi/10.1039/b101332g
関連情報URL(IsPartOf)http://www.rsc.org/Publishing/Journals/P1/Index.asp
著者版/出版社版その他
リポジトリID2008010201
地域区分山口大学
URIhttp://www.lib.yamaguchi-u.ac.jp/yunoca/handle/2008010201