524022-76-2Relevant articles and documents
Synthesis of 3-substituted-4-hydroxyquinoline N-oxides from the Baylis-Hillman adducts of o-nitrobenzaldehydes
Lee, Ka Young,Kim, Jeong Mi,Kim, Jae Nyoung
, p. 385 - 390 (2003)
The reaction of the Baylis-Hillman adducts 1b-f derived from o-nitrobenzaldehydes in trifluoroacetic acid in the presence of triflic acid (0.2equiv.) afforded 3-substituted-4-hydroxyquinoline N-oxides 2b-e and 2a in good to moderate yields. The reaction mechanism was evidenced by the experiment with 1f, the Baylis-Hillman adduct of 2-nitrobenzaldehyde N-tosylimine, as the one involving N-hydroxyisoxazoline as the key intermediate.
The Baylis-Hillman approach to quinoline derivatives
Familoni, Oluwole B.,Klaas, Phindile J.,Lobb, Kevin A.,Pakade, Vusumzi E.,Kaye, Perry T.
, p. 3960 - 3965 (2008/09/18)
Baylis-Hillman reactions of 2-nitrobenzaldehydes with various activated alkenes afford adducts that undergo reductive cyclisation to quinoline derivatives. The chemo- and regioselectivity of cyclisation appears to be influenced by the choice of both the substrate and the reagent system, and competing reactions have been observed. The Royal Society of Chemistry 2006.
