Cooperative Heterogeneous Organocatalysis and Homogeneous Metal Catalysis for the One‐Pot Regioselective Synthesis of 2‐Pyridones

Abstract

International audienceA direct, one-pot and regioselective access to N-alkyl- and N-aryl-substituted 2-pyridones is described from readily available β-ketoamides and either primary or secondary propargyl alcohols. This approach involves the combination of two different cooperative homogeneous and heterogeneous catalytic systems based on a transition metal oxide and a supported organocatalyst, respectively

Synthesis and Anti-Trypanosoma cruzi Biological Evaluation of Novel 2-Nitropyrrole Derivatives

“…LC/MS monitoring of this reaction revealed the disappearance of the starting product signal and the absence of formation of the desired products 3 or 4 . A reaction optimization using LC/MS monitoring was therefore conducted by varying different parameters according to amidification protocols described in the literature ( Table 1 ) [ 19 ]. The various attempts were not conclusive, and we never observed the expected product 3 or 4 by LC/MS monitoring.…”

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

“…Afterward, they can extend the substrate scope to alkynyl alcohols 34b instead related aldehydes ( Scheme 47 ). 59 β-keto amide 34a underwent the reaction with alkynyl alcohol 34b in refluxing THF for 12 hours using 10 mol% of P-BEMP (phosphazene-supported organocatalyst and RuO 2 · x H 2 O as an oxidizing catalyst. A possible mechanism is shown in Scheme 48 .…”

The applications of β‐keto amides for heterocycle synthesis

“…Constantieux and co‐workers developed a cooperative polymer‐supported organocatalysis (P‐BEMP) and homogeneous metal catalysis for the one‐pot synthesis of N ‐alkyl‐ and N ‐aryl‐substituted 2‐pyridones 246 from β ‐keto amides 13 and propargylic alcohols 245 with excellent regioselectivity and generality (Scheme 64) [119]. Maiti and collaborators reported the FeCl 3 •6H 2 O catalyzed condensation between β ‐keto amides and aryl and aliphatic aldehydes, affording the trans ‐isomers of dihydro‐2‐pyridone derivatives in good to excellent yields [120].…”