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■ Variation of Skeletons of Antitumor Antibiotics I. Simple Synthesis of Naphtho[2,3-g]quinolines and a Naphtho[2,3-g]quinoxaline

Noriichi Oda, Kazuhiro Kobayashi, Taisei Ueda, and Isoo Ito*

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

Simple synthesis of naphtho[2,3-g]quinolines (III,VI,IX) and a naphtho[2,3-g]quinoxaline (XII), which are a novel heterocyclic ring system, was carried out by the Diels-Alder reaction of 1,2-dimethylenecyclohexane (I) with quinoline-5,8-quinone (II,V,VIII) or quinoxaline-5,8-quinone (XI). Air oxidation of these adducts (III,VI,IX) in alcoholic alkaline solution gave tetrahydronaphtho[2,3-g]quinolines (IV,VII,X).