Landscaping of Quinoline based Heterocycles as Potential Antimicrobial Agents: A Mini Review

Desai, N. C.

doi:10.19080/napdd.2017.01.555570

Cited by 8 publications

(1 citation statement)

References 22 publications

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“…Quinolines express a multitude of biological activities and are valuable in the treatment of malaria [21][22][23][24][25][26][27] and other tropical diseases (e.g., Chagas disease, human African trypanosomiasis and leishmaniasis) [28] as well as tuberculosis [29], cancer [30,31] and bacterial infections [32]. Several quinoline-based drugs have been known for many years, while others are more experimental in nature.…”

Section: Introductionmentioning

confidence: 99%

Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines

Fobi

Bunce

2022

Molecules

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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(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.

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