Tetrahedron

Novel functionalization of 1-methyl-2-quinolone; dimerization and denitration of trinitroquinolone

N Nishiwaki, M Sakashita, M Azuma, C Tanaka…

Index: Nishiwaki, Nagatoshi; Sakashita, Midori; Azuma, Mayumi; Tanaka, Chitose; Tamura, Mina; Asaka, Noriko; Hori, Kazushige; Tohda, Yasuo; Ariga, Masahiro Tetrahedron, 2002 , vol. 58, # 3 p. 473 - 478

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Citation Number: 15

Abstract

New methods for functionalization of 1-methyl-2-quinolone (MeQone) skeleton are provided. The reaction of 1-methyl-3, 6, 8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6, 8-dinitroquinolone (6, 8-DNQ). Dimerization predominantly proceeds at room temperature, and denitration takes place under heated and diluted conditions. We also provide a plausible mechanism for these reactions on the basis of structure–reactivity ...