1111748-75-4Relevant academic research and scientific papers
Straightforward strategy for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman adducts by 1,3-dipolar cycloaddition and reductive cyclization
Singh, Virender,Singh, Vijay,Batra, Sanjay
experimental part, p. 5446 - 5460 (2009/05/11)
A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis-Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives proceeded efficiently in the presence of In/HCl, whereas similar reductions of pyrazolines gave better yields when carried out in the presence of an Fe/AcOH mixture. However, similar attempts employing the Baylis-Hillman adduct of 2-nitrobenzaldehyde and methyl vinyl ketone did not yield the desired compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
