Fobi, Kwabena; Bunce, Richard A. published the artcile< Domino Nitro Reduction-Friedlander Heterocyclization for the Preparation of Quinolines>, Name: Ethyl 3-oxo-3-phenylpropanoate, the main research area is quinoline preparation; aminobenzaldehyde activated ketone domino nitro reduction Friedlander heterocyclization; Friedländer synthesis; dissolving metal reduction; domino reaction; heterocyclization; quinolin-2(1H)-ones; quinolines.
The Friedlander synthesis offers efficient access to substituted quinolines from 2-aminobenzaldehydes and activated ketones in the presence of a base. The disadvantage of this procedure lies in the fact that relatively few 2-aminobenzaldehyde derivatives are readily available. To overcome this problem, authors report a modification of this process involving the in situ reduction of 2-nitrobenzaldehydes with Fe/AcOH in the presence of active methylene compounds (AMCs) to produce substituted quinolines in high yields. The conditions are mild enough to tolerate a wide range of functionality in both reacting partners and promote reactions not only with Ph and benzyl ketones, but also with β-keto-esters, β-keto-nitriles, β-keto-sulfones and β-diketones. The reaction of 2-nitroarom. ketones with unsym. AMCs is less reliable, giving a competitive formation of substituted quinolin-2(1H)-ones from the cyclization of the Z Knoevenagel intermediate which appears to be favored when certain large groups are adjacent to the AMC ketone carbonyl.
Molecules published new progress about Benzaldehydes Role: RCT (Reactant), RACT (Reactant or Reagent) (nitro). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Name: Ethyl 3-oxo-3-phenylpropanoate.
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