Abstract
2‐Aminobenzaldehydes as Versatile Substrates for Rhodium‐Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis
Highlights
Given the importance of nitrogen-containing molecules to a great number of applications, we were attracted to the idea of developing a simple, readily available family of aldehydes that feature N-chelation for intermolecular hydroacylation reactions
Using 2-(pyrrolidin-1-yl)benzaldehyde 8 a and 1-hexyne as the test substrates, we evaluated a number of Rh-based catalysts (Table 1)
With suitable reaction conditions in hand, we explored the variation of the 2-aminobenzaldehyde component in reactions with phenylacetylene (Scheme 2)
Summary
We demonstrate that simple and readily available 2-aminobenzaldehydes are excellent substrates for intermolecular Rh-catalyzed alkyne hydroacylation, and in doing so add to the motifs available for use in these valuable processes. The products of these reactions, amino-substituted enones, were directly converted into a series of useful dihydroquinolone heterocycles.
Sign-in/Register to view highlights & summary 
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call