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Synthesis of Highly Functionalized Bis(4H-chromene) and 4H-Benzo[g]chromene Derivatives via an Isocyanide-Based Pseudo-Five-Component Reaction

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journal contribution
posted on 05.06.2009, 00:00 by Ahmad Shaabani, Rahim Ghadari, Afshin Sarvary, Ali Hossein Rezayan
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 CH3CN 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.