Shaabani Ahmad, Ghadari Rahim, Sarvary Afshin, Rezayan Ali Hossein
Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran.
J Org Chem. 2009 Jun 5;74(11):4372-4. doi: 10.1021/jo9005427.
The reactive intermediates generated by the addition of alkyl, aryl, and alicyclic isocyanides to dialkyl acetylenedicarboxylates were trapped by 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione or 2-hydroxynaphthalene-1,4-dione to produce highly functionalized bis(4H-chromene)- and 4H-benzo[g]chromene-3,4-dicarboxylate derivatives in fairly good yields in CH(3)CN at room temperature. These compounds are closely related to the ring systems pentalongin, dehydroherbarin, 1,3-disubstituted-3,4-dehydropyranonaphthoquinones, and 3-arylpyranonaphthoquinones, which have a broad spectrum of biological activity.
通过将烷基、芳基和脂环族异氰化物添加到二烷基乙炔二羧酸酯中生成的反应中间体，被2,5 - 二羟基环己 - 2,5 - 二烯 - 1,4 - 二酮或2 - 羟基萘 - 1,4 - 二酮捕获，在室温下于乙腈中以相当高的产率生成高度官能化的双(4H - 色烯) - 和4H - 苯并[g]色烯 - 3,4 - 二羧酸酯衍生物。这些化合物与五环菌素、脱氢草菌素、1,3 - 二取代 - 3,4 - 脱氢吡喃萘醌和3 - 芳基吡喃萘醌的环系密切相关，它们具有广泛的生物活性。
