1448544-55-5Relevant articles and documents
NHC-Cu(I)-Catalyzed Friedl?nder-Type Annulation of Fluorinated o-Aminophenones with Alkynes on Water: Competitive Base-Catalyzed Dibenzo[b,f][1,5]diazocine Formation
Czerwiński, Pawe?,Michalak, Micha?
, p. 7980 - 7997 (2017)
An efficient, easily scalable synthesis of 4-trifluoromethylquinolines and naphthydrines (as well as their difluoro- and perfluoro-analogues) as a result of tandem direct catalytic alkynylation/dehydrative condensation of o-aminofluoromethylketones (o-FMKs), for the first time catalyzed by NHC-copper(I) complexes on water, is reported. A wide range of terminal alkynes is tolerated under the reaction conditions, including β-lactam-, steroid-, and sugar-derived ones, leading to desired quinolines and naphthydrines with good yields. Further investigations proved that o-FMKs could be efficiently transformed into a rare class of heterocyclic compounds - dibenzo[b,f][1,5]diazocines - by a base-catalyzed condensation, also on water. The developed method was applied for gram-scale synthesis of a fluorinated analogue of G protein-coupled receptor antagonist (GPR91).
Proline potassium salt: A superior catalyst to synthesize 4-trifluoromethyl quinoline derivatives via Friedlander annulation
Du, Xiao Long,Jiang, Biao,Li, Yuan Chao
, p. 7481 - 7486 (2013/08/23)
Proline potassium salt was successfully firstly used to catalyze the Friedlander annulation toward the synthesis of 4-trifluoromethyl-substituted quinolines from the substituted 2-trifluoroacetyl anilines and variety carbonyl compounds under mild conditions in good to excellent yields. This catalyst provides several advantages, such as shorter reaction time, high regioselectivity, functional group tolerance, and broad substrate scope.
