5209-25-6Relevant articles and documents
Manganese(III)-Mediated Oxidative Radical Cyclization 2. Reaction of 1,1,ω,ω-Tetraarylsubstituted Terminal Alkadienes with Malonamide or Acetoacetamide
Nishino, Hiroshi,Hashimoto, Hideaki,Korp, James D.,Kurosawa, Kazu
, p. 1999 - 2010 (1995)
The oxidation of 1,1,6,6-tetraaryl-1,5-hexadienes with manganese(III) acetate in the presence of malonamide gave two types of 5-exo cyclization products, 1-carbamoyl-8-diarylmethylene-3-azabicyclooctan-2-ones and 3,10-dioxatricyclo1,5>undecane-2,11-diones, in good to moderate yields.Similar reactions of 1,1,5,5-tetraaryl-1,4-pentadienes or 1,1,7,7-tetraaryl-1,6-heptadienes with malonamide yielded only complex mixtures, except for the formation of a small amount of 3,11-dioxatricyclo1,5>dodecane-2,12-dione.On the other hand, 1,1,5,5-tetraaryl-1,4-pentadienes reacted with acetoacetamide in the presence of manganese(III) acetate to afford 3-carbamoyl-2-methyl-4-(2-propenyl)-4,5-dihydrofurans and 1,4-pentadienes substituted at the 3-position with acetoacetamide.A similar reaction of 1,1,6,6-tetraaryl-1,5-hexadienes with acetoacetamide gave 8--3-oxabicyclooctan-2-ones, 1-acetyl-8-diarylmethylene-3-azabicyclooctan-2-ones, and 4-(3-butenyl)-3-carbamoyl-2-methyl-4,5-dihydrofurans.The selectivity of the inter- and intramolecular cyclizations containing the carboxamide moiety of malonamide or acetoacetamide is discussed.