New Entries to 3‐Acylchromones: TM‐Catalysed Decarboxylative Cross‐Coupling of α‐Keto Acids with ortho‐Hydroxyarylenaminones, 2,3‐Unsubstituted Chromones and 3‐Iodochromones.

Mkrtchyan, Satenik; Iaroshenko, Viktor O.

Herein we report three new synthetic routes for the construction of a 3‐acyl‐substituted chromone scaffold by employing an acylation of ortho‐hydroxyarylenaminones, 2,3‐unsubstituted chromones and 3‐iodochromones through decarboxylative C–C cross‐coupling with α‐keto acids. This study indicates that the title transformations can be effectively catalysed by a set of silver and palladium salts. However, maximum efficiency in terms of overall yields was reported for the route starting from ortho‐hydroxyarylenaminones. The scope of this methodology was thoroughly studied. It indicated a synthesis of 26 chromone derivatives in good to excellent yields. Three new entries to 3‐acylchromones utilizing transition metal catalyzed decarboxylative cross‐coupling reactions of α‐keto acids with ortho‐hydroxyenaminones, 2,3‐unsubstituted chromones and 3‐iodochromones are reported. The title methodologies permit a concise synthesis of series of drug‐like chromone derivatives and are suitable for the combinatorial preparation of compounds libraries.

CHROMONES; PALLADIUM catalysts; DECARBOXYLATION; COUPLING reactions (Chemistry); KETONIC acids; ACYLATION

European Journal of Organic Chemistry, 2018, Vol 2018, Issue 48, p6867

1434-193X

Academic Journal

10.1002/ejoc.201801231