Tetrahedron

Reactive 2-quinolones dearomatized by steric repulsion between 1-methyl and 8-substituted groups

…, K Kobiro, H Asahara, K Kakiuchi, R Sugimoto, K Saigo…

Index: Chen, Xin; Kobiro, Kazuya; Asahara, Haruyasu; Kakiuchi, Kiyomi; Sugimoto, Ryuichi; Saigo, Kazuhiko; Nishiwaki, Nagatoshi Tetrahedron, 2013 , vol. 69, # 23 p. 4624 - 4630

Full Text: HTML

Citation Number: 6

Abstract

Usual 1-methyl-2-quinolone (MeQone) derivatives are not reactive because of aromatic property in the heterocyclic ring. On the other hand, 8-substituted MeQones have been proved to be highly reactive, which is caused by steric repulsion between the 1-methyl and the 8-substituted groups. When 1-methyl-3, 6, 8-trinitro-2-quinolone was treated with potassium (or trimethylsilyl) cyanide, cyanation proceeded at the 4-position ...