Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 6, Pages 1940-1945Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob02400e
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Funding
- DST [SB/S1/OC-19/2013]
- UGC
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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 beta-keto esters/1,3-dicarbonyls and alpha-arylacetylenyl-beta-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.
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