DABCO catalyzed domino Michael/hydroalkoxylation reaction involving α-alkynyl-β-aryl nitroolefins: excellent stereoselective access to dihydropyrano[3,2-c]chromenes, pyranonaphthoquinones and related heterocycles

Abstract

Excellent stereoselective (up to ≤96 : 4 Z/E ratio) construction of pharmaceutically interesting functionalized pyrano[3,2-c]chromenes, pyranonaphthoquinones and related pyrano-fused heterocycles has been achieved in good to high yields (72–89%) through a domino Michael/hydroalkoxylation reaction involving several enolizable cyclic β-keto esters/1,3-dicarbonyls and α-arylacetylenyl-β-nitrostyrenes as binucleophiles in EtOH at room temperature using DABCO as an organocatalyst. Moreover, syn-2-benzyl-4-aryl-3,4-dihydropyrano[3,2-c]chromenes were obtained in high yields (81–86%) via a stereoselective denitrohydrogenation of the corresponding 2-benzylidene-3,4-dihydropyrano[3,2-c]chromenes using a catalytic amount of 10% Pd/C.