Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

Abstract

SummaryHerein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.

Silver‐Mediated Synthesis of 4H‐Benzoxazin‐4‐ones by Intramolecular Decarboxylative O‐Acylation Reactions with α‐Oxocarboxylic Acid

“…During the preparation of this manuscript, the Gogoi group published the copper‐catalyzed C–N, C–O coupling reaction of arylglyoxylic acids with isatins. Earlier, we demonstrated a sequential decarboxylative coupling reaction for the synthesis of polycyclic triazoles . Taking advantage of our previous experience with decarboxylative coupling reactions, we herein describe the development of a new approach to the synthesis of 4 H ‐benzoxazin‐4‐ones, which involves an intramolecular decarboxylative O ‐acylation reaction with an α‐oxocarboxylic acid (Scheme ).…”

“…Earlier, we demonstrated a sequential decarboxylative coupling reaction for the synthesis of polycyclic triazoles. [15] Taking advantage of our previous experience with decarboxylative coupling reactions, we herein describe the development of a new approach to the synthesis of 4H-benzoxazin-4ones, which involves an intramolecular decarboxylative O-acylation reaction with an α-oxocarboxylic acid (Scheme 1). This is the first intramolecular approach for a decarboxylative acylation reaction.…”

Controlled photorelease of alkynoic acids and their decarboxylative deprotection for copper-catalyzed azide/alkyne cycloaddition

“…Indeed, free 2alkynoic acids react with organic azides upon decarboxylation with similar regioselectivity to that of the corresponding terminal alkynes. [13][14][15][16][17] Heating or a metal, 18 typically Cu I , 17 catalysis is usually required for a successful decarboxylation. 19,20 The controlled release of molecules from photoremovable protecting groups (PPGs; caged groups) has the advantage in spatial and temporal delivery of a great variety of active reagents.…”