Tetrahedron

Cycloaddition reactions of N-alkoxycarbonyl-4-quinolones

JR Nicholson, G Singh, KJ McCullough, RH Wightman

Index: Nicholson, John R.; Singh, Gurdial; McCullough, Kevin J.; Wightman, Richard H. Tetrahedron, 1989 , vol. 45, # 3 p. 889 - 908

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Citation Number: 6

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 ( ...