Time‐Efficient Synthesis of Pyrido­[2,3‐d]pyrimidinones via α‐Oxoket­enes

Abstract

α‐Oxoketene reactive intermediates generated in situ by microwave‐assisted Wolff rearrangement of 2‐diazo‐1,3‐dicarbonyl compounds have been found to react with 6‐aminopyrimidine derivatives as 1,3‐C,N‐bis‐nucleophiles to yield pyrido[2,3‐d]pyrimidinones and related compounds amenable to further functionalization.

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

“…Raminelli et al applied this method in the O-arylation of sterically hindered 2,6-dihalophenols . In addition, O-arylation of phenols was also reported by other groups. , Unfortunately, the Larock’s method was not applicable to both alcohols and aliphatic carboxylic acids at the moment. Until 2015, Chen, Zhang, and co-workers could solve this inactivity problem on aliphatic carboxylic acids.…”

Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines

“…Diazo carbonyl compounds were also used as ketene sources for the α-ketoacylation of pyrazoles via CH insertion under microwave activation . The same reaction conditions were applied for the annulation of 2-aminopyrazole or 2-(alkylideneamino)­pyrazoles with cyclic 2-diazo-1,3-dicarbonyl compounds. Recently, the Ni­(II)-catalyzed reaction of α-diazo pyrazoleamides with sulfides proceeding with the retention of the pyrazole system was reported .…”

Recent Advances in Pd‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reactions with Triflates or Nonaflates

“…With PdCl 2 (dppf) as a catalyst and Cs 2 CO 3 as a base in a THF/H 2 O (6:1) mixture at 70 °C the authors were able to synthesize the desired cross‐coupled product 121 in 77% yield (Scheme 38). [56] …”