Synthesis of highly functionalized bis(4H-chromene) and 4H-benzo[g]chromene derivatives via an isocyanide-based pseudo-five-component reaction.
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.
Shaabani
Ahmad
A
Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran. a-shaabani@cc.sbu.ac.ir
Ghadari
Rahim
R
Sarvary
Afshin
A
Rezayan
Ali Hossein
AH
D001578:Benzopyrans / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D013329:Structure-Activity Relationship
D001578:Benzopyrans; D002264:Carboxylic Acids; D003486:Cyanides