Tetrahedron Letters p. 2211 - 2214 (1997)
Update date:2022-08-28
Topics:
Behforouz, Mohammad
Gu, Zhengxiang
Stelzer, Lindsay S.
Ahmadian, Mohammad
Haddad, Jalal
Scherschel, John A.
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.
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