%0 Journal Article
%T Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
%A S¨˘ Marcus M.
%J Journal of the Brazilian Chemical Society
%D 2003
%I Sociedade Brasileira de Qu¨Şmica, SBQ
%X The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described.
%K allylic azides
%K 3-carbomethoxyquinoline
%K N-allylic imines
%K Staudinger/aza-Wittig reaction
%K Baylis-Hillman reaction
%U http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018