- 著者
- 小林 和弘 織田 範一 伊藤 磯雄
- 出版者
- 公益社団法人 日本薬学会
- 雑誌
- YAKUGAKU ZASSHI (ISSN:00316903)
- 巻号頁・発行日
- vol.101, no.9, pp.806-813, 1981-09-25 (Released:2008-05-30)
- 参考文献数
- 14
- 被引用文献数
- 1 1
As the initial study of variations of skeletons of antitumor antibiotics, simple synthesis of naphtho [2, 3-g] quinolines (IIIa, b, VIII) and naphtho [2, 3-g] quinoxalines (XIIIa, b), which are novel heterocyclic ring systems, was carried out by Diels-Alder reaction of 1, 2-dimethylenecyclohexane with quinoline-5, 8-diones (Ia-c) or quinoxaline-5, 8-diones (IIa, b). Air oxidation of these Diels-Alder adducts gave tetrahydro naphtho [2, 3-g] quinolines (IVa, b, IX) and tetrahydronaphtho [2, 3-g] quinoxalines (XVa, b). The Diels-Alder adducts and aromatized compounds were converted into the corresponding diacetoxynaphtho [2, 3-g] quinolines (VI, VII, X) and diacetoxynaphtho [2, 3-g] quinoxalines (XVII, XVIII).
- 著者
- 織田 範一 小林 和弘 植田 泰誠 伊藤 磯雄
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.26, no.8, pp.2578-2581, 1978-08-25 (Released:2008-03-31)
- 被引用文献数
- 1 3
Diels-Alder reaction of 5-nitro-1, 4-naphthoquinone (1) and unsymmetrical butadienes was carried out. Reaction of 1 and 2-methyl-1, 3-butadiene gave 1, 4, 4a, 9a-tetrahydro-2-methyl-5-nitro-anthraquinone (2) and its 3-methyl analogue (3) at the ratio of 9.2 : 1. Reaction of 1 and 1, 3-pentadiene gave 1, 4, 4a, 9a-tetrahydro-1-methyl-8-nitroanthraquinone (8) and its 5-nitro analogue (9) at the ratio of 10 : 7. Their structures have been determined by aromatization to methyl-nitroanthraquinones.