Diels-Alder reactions of N-silyloxy 1-azadienes

Article abstract of DOI:10.1016/S0040-4039(97)00326-2

Novel 1-(t-butyldimethyisilyloxy)-1-aza-1,3-butadienes 1 and 2 are prepared by the reaction of O-(t-butyldimethylsilyloxy)hydroxylamine with methyl vinyl ketone and methacrolein, respectively. Azadienes 1 and 2 through sharing of oxygen nonbonding electrons are activated and thus their Diels-Alder reactions with a number of halobenzoquinones, napthoquinones and N-phenylmaleimide regiospecifically give low to good yields of various pyridine heterocycles.