Cascade C–N bond cleavage of amides/intramolecular amination reactions: an atom economical way to α-cabolin-4-ones

Abstract

An atom economical approach for the synthesis of α-carbolin-4-ones has been developed. This process was realized via C-N bond cleavage/intramolecular amination cascade. During this process, one C-N and one C-C...

Diastereoselective Synthesis of Bicyclo[3.3.0]octenones by Copper-Catalyzed Transannular Ring-Closing Reaction

“…The carbonyl group at the indole C3 position remained unreacted. This may due to the electron-donating conjugation effect of the N atom on the indole ring, which decreases the activity of the carbonyl group …”

dppb and TfOH promoted cascade reaction of o-nitrophenylpropiolamides to access C2-spiro-pseudoindoxyls

“…17 However, the reduction of 2a with NaBH 4 or NaOEt failed, and only a complex reaction mixture was observed. 18 We also attempted the Wittig olefination of 2a , but no reaction occurred, and the raw materials remained. 19…”

Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation

“…18 However, despite a plethora of N -arylation reactions documented in the literature, the use of amides for the production of N -heterocyclic compounds via C–N bond cleavage is rare. 19 In continuation of our previous work on the synthesis of N-heterocyclic compounds, 20 we herein report the first CuI-catalyzed cascade cyclization/hydrodehalogenation sequence for quinazoline synthesis, in which acetamide and H 2 O are used as nitrogen and hydrogen sources, respectively (Scheme 1e). Importantly, this protocol provides an expeditious synthesis of deuterium-labeled quinazolines under one-pot tandem reaction conditions.…”