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J Org Chem. 2009 Jun 5;74(11):4372-4. doi: 10.1021/jo9005427.

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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  • 1Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran.


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.

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