Cycloaddition reactions of N-alkoxycarbonyl-4-quinolones

John R. Nicholson, Gurdial Singh, Kevin J. McCullough, Richard H. Wightman

Research output: Contribution to journalArticle

Abstract

3-Ethoxycarbonyl-4-1(H)-quinolone (2) and 3-nitro-4-1(H)-quinlone (3) reacted with a variety of chloroformates to give the N-acyl-3-ethoxycarbonyl-4-1(H)-quinolones (4a-4d) and N-acyl-3-nitro-4-1(H)-quinolones (5a,b) respectively. Reaction of (4a,b,d) with 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (6) gave the respective[4+2]cycloadduct,5,10a-diethoxycarbonyl-3,10-dioxo-1-methoxy-octahydroacridine(7a)and the analogues (7b,d). Treatment of (5a,b) with the above diene gave rise to two cycloadducts 3,10-dioxo-5-ethoxycarbonyl-1-methoxy-10a-nitro-octahydroacridines which had arisen from addition from the exo and endo transistion states. The quinolones (4a,b) on reaction with Gessons diene (12) and the ketene acetals (15) and (16), afforded Michael adducts 2-[1,3-biscarboethoxy-1,2-dihydroquinolin-2-yl-4-hydroxy]-methyl-1-carboethoxy-4-methoxycyclohexa-1,3-diene (14a), and (14b),(17),(18) respectively. Base treatment of (14a,b) gave the aminoketone 7-(2'-aminobenzoyl)-8-hydroxy-3-methoxy-1,2-dihydronaphthalene (19) which was acetylated to afford (20). The latter could be selectively O-deacetylated to give 7-(2'-acetamidobenzoyl)-8-hydroxy-3-methoxy-1,2-dihydronaphthalene (21). © 1989.

Original languageEnglish
Pages (from-to)889-908
Number of pages20
JournalTetrahedron
Volume45
Issue number3
Publication statusPublished - 1989

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    Nicholson, J. R., Singh, G., McCullough, K. J., & Wightman, R. H. (1989). Cycloaddition reactions of N-alkoxycarbonyl-4-quinolones. Tetrahedron, 45(3), 889-908.