Indium-mediated 1,2,4,5-hexatetraen-3-ylation of 4-acetoxy-2-azetidinones and their applications to the Diels-Alder reactions for the synthesis of 2-azetidinone derivatives.
4-Acetoxy-2-azetidinones reacted with organoindium reagent generated in situ from indium and 1,6-dibromo-2,4-hexadiyne in the presence of LiCl in DMF to selectively produce 2-azetidinones possessing 1,2,4,5-hexatetraen-3-yl group on the C4-position. The Diels-Alder reactions of 4-(1,2,4,5-hexatetraen-3-yl)-2-azetidinones with a variety of dienophiles and subsequent aromatizations afforded valuable functional group-substituted 2-azetidinones in good yields.
National Research Laboratory for Catalytic Organic Reaction, Department of Chemistry and Institute for Molecular Science & Fusion Technology, Kangwon National University, Chunchon 200-701, Republic of Korea.
Heashim
H
Yu
Phil Ho
PH
Lee
D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure
D001384:Azetidines; D007204:Indium