85020-83-3Relevant academic research and scientific papers
Steric and Electronic Requirements in the Synthesis of 2,3-Dihydro-4(1H)-quinolinones by the Tandem Michael-SNAr Reaction
Bunce, Richard A.,Nago, Takahiro,Abuskhuna, Suaad
, p. 1143 - 1149 (2015)
The steric and electronic requirements have been investigated for the synthesis of 2,3-dihydro-4(1H)-quinolinones by the tandem Michael-SNAr reaction. Substrates bearing a single methyl group at the β-enone carbon gave excellent yields of the title compounds from both the E and Z isomers with X=H or NO2. Substrates with β,β-dimethyl substitution at the Michael terminus gave low yields of heterocyclic products in molecules having monoactivated SNAr aromatic acceptor rings (X=H) and very good yields for diactivated systems (X=NO2). For these hindered substrates, success in the final cyclization hinges on the ability of the aromatic acceptor to capture the pendant nitrogen nucleophile of the initial Michael adduct before this intermediate can revert to starting materials.
Preparation of 5-nitro-2-amino[b]thiophenes and 1-(2-amino-5-nitrophenyl) ethanones via microwave irradiation
Rais, Afsha,Ankati, Haribabu,Biehl, Ed
experimental part, p. 599 - 602 (2009/11/30)
(Chemical Equation Presented) 1-(2-Chloro-5-nitrophenyl)ethanone) reacts with various amines in the presence of sulfur under microwave radiation to give the corresponding 2-aminobenzo[b]-thiophenes 3a-f in good yields. The yields of 3a-f are vastly superi
