Preparações e aplicações sintéticas recentes de enaminonas

Abstract

Dedicamos este artigo ao Prof. Dr. Sílvio do Desterro Cunha, da UFBA, pelo constante estímulo, esperando contribuir com mais uma "inevitável" leitura para seu grupo de pesquisa.

One‐Step Synthesis of 3,4‐Diphenyl‐2‐pyrrolinones by Solvent‐Free and Bi2O3‐Catalyzed Approaches and Cytotoxicity Screening Against Glioma Cells

“…Acyclic enaminones are attractive as building blocks to the synthesis of polysubstituted heterocycles, because they can be easily prepared from 1,3-dicarbonyl compounds, among other precursors [14][15][16][17][18][19][20][21][22][23][24]. In this scenario, the formal aza- [3 + 2] cycloaddition of enaminones emerges as a versatile strategy to the preparation of five-membered N-heterocycles because two sigma bonds are formed in a single step, and catalysis by metal salts and metal-free annulations have already been reported [25][26][27][28][29][30][31][32] (Fig.…”

“…Despite the diversity of approaches that employ the formal aza-[3 + 2] cycloaddition of enaminones 1 as a direct route to 2-pyrrolinone [18][19][20]22,[24][25][26][27][28][29][30][31][32], the one-step synthesis of such δ-lactam with two vicinal phenyl substituents is still scarce. On the other hand, the use of diphenylcyclopropenone 2 is strategic when two adjacent phenyl rings are required in planned targets [33][34][35][36].…”

Synthesis of Acyclic -Enaminones Through Reaction of Enones and Benzyl Azide

“…The synthesis of enaminones is a theme of ongoing interest 1 because this class of compound is a versatile intermediate in organic synthesis 2 as well as due to their biological activity. 3 Enaminones are molecules with the conjugated system N-C=C-C=O, and the amine and acyl group lead these compounds to have both reactive effects: electrophilic (blue) and nucleophilic (red).…”

Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

“…For this reason, enaminones have found a wide application in the synthesis of various heterocycles, dyes and drugs. 22,[30][31][32] Specifically, we have described the synthesis of N- [1-aryl(alkyl)-3-oxo-4,4,4-trifluoro(chloro) 29 The purpose of this paper is to report the complete results of the reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones (1a-j) with 1,3-phenylenediamine to obtain a wide series of ten examples of trifluoroacetyl substituted 1,3-phenylene-bis-enamines (2a-j) and also to investigate the chemical behavior of alkyl, aryl and heteroaryl-substituted enamino intermediates (2) for their application in the simultaneous regioselective synthesis of new 2,8-or 4,8-bis(trifluoromethyl)-2,10-bis-alkyl(aryl)-1,7-phenanthrolines (3) and the respective 4-(trifluoromethyl)-7-aminoquinolines (4) under similar reaction conditions as described previously.…”