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Paper | Regular issue | Vol 43, No. 10, 1996, pp.2139-2152
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7525
Studies on Nitrogen-containing Heterocyclic Compounds. Novel Synthesis of Naphtho[1,2-b and 2,1-b][1,8]naphthyridines and Oxidation Reactions with Peroxy Acids

Isao Takeuchi, Koosuke Asai, Yoshiki Hamada, Katsuyoshi Masuda, Hiroko Suezawa, Minoru Hirota, Yukihisa Kurono, and Keiichiro Hatano

*Faculty of Pharmacy, Meijo University, 150 Yagoto, Tempaku-ku, Nagoya, Aichi 468-8503, Japan

Abstract

A modified Friedländer condensation of 2-aminonicotinaldehyde with α- and β-naphthols lead successfully to two new naphtho[1,2-b and 2,1-b][1,8]naphthyridines in a single synthetic procedure. The oxidation of the naphthonaphthyridines with peroxy acids afforded novel products such as a seven-membered oxazepine moiety. Structures were characterized by standard spectroscopy. The crystal and molecular structures (3) and (4) were determined by X-ray analyses.