ArticleMolecules (Basel, Switzerland)2022
Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines.
Article in Molecules (Basel, Switzerland), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed, 4 citations in OpenAlex.
- Reductive Cyclization ofMolecules (Basel, Switzerland) · 2026Article
- Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involvingBeilstein journal of organic chemistry · 2023Article
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2 authors at 1 institution in 1 country.
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Abstract
The Friedländer 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, we 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 phenyl and benzyl ketones, but also with β-keto-esters, β-keto-nitriles, β-keto-sulfones and β-diketones. The reaction of 2-nitroaromatic ketones with unsymmetrical AMCs is less reliable, giving a competitive formation of substituted quinolin-2(1
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