Trifluoroacetic Acid: A More Effective and Efficient Reagent for the Synthesis of 3‐Arylmethylene‐3,4‐dihydro‐1H‐quinolin‐2‐ones and 3‐Arylmethyl‐2‐amino‐quinolines from Baylis—Hillman Derivatives via Claisen Rearrangement.

doi:10.1002/CHIN.200721128

Paper

Trifluoroacetic Acid: A More Effective and Efficient Reagent for the Synthesis of 3‐Arylmethylene‐3,4‐dihydro‐1H‐quinolin‐2‐ones and 3‐Arylmethyl‐2‐amino‐quinolines from Baylis—Hillman Derivatives via Claisen Rearrangement.

Published Jan 8, 2007 · Richa Pathak, Sudharshan Madapa, S. Batra

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Abstract

Abstract Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclization reaction to yield 3-arylmethylene-3,4-dihydro-1 H -quinolin-2-ones from compounds obtained from the S N 2 reaction between anilines and acetyl derivatives of Baylis–Hillman adducts of acrylates in the presence of DABCO. In contrast, similar compounds obtained from the acetyl derivatives of Baylis–Hillman adduct of acrylonitrile on treatment with trifluoroacetic acid directly furnish 3-arylmethyl-2-amino-quinoline via tandem Claisen rearrangement, cyclization and isomerization.

Study Snapshot

Trifluoroacetic acid is an efficient reagent for synthesizing 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis-Hillman derivatives via Claisen rearrange

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Trifluoroacetic Acid: A More Effective and Efficient Reagent for the Synthesis of 3‐Arylmethylene‐3,4‐dihydro‐1H‐quinolin‐2‐ones and 3‐Arylmethyl‐2‐amino‐quinolines from Baylis—Hillman Derivatives via Claisen Rearrangement.

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References

An alternate approach to quinoline architecture via Baylis–Hillman chemistry: SnCl2-mediated tandem reaction toward synthesis of 4-(substituted vinyl)-quinolines

SnCl2-mediated tandem reaction allows for the synthesis of densely substituted quinolines from Baylis-Hillman adducts, resulting in 4-(substituted vinyl)-quinolines.

Bactericidal Activities of R207910 and Other Newer Antimicrobial Agents against Mycobacterium leprae in Mice

R207910 shows equal bactericidal activity against Mycobacterium leprae as rifapentine, rifampin, or moxifloxacin, suggesting potential for leprosy treatment.

Chemical transformation of Baylis-Hillman adducts: The reaction of methyl 3-arylamino-2-methylene-3-phenylpropanoates in polyphosphoric acid

Baylis-Hillman adducts can be used to synthesize various compounds with interesting skeletons, such as 3-benzylquinolin-2-one, 4-amino-2-benzylideneindan-1-one, and 1-amino-9a,10-dihydr

A Diarylquinoline Drug Active on the ATP Synthase of Mycobacterium tuberculosis

R207910 is a promising new tuberculosis drug that effectively inhibits both drug-sensitive and drug-resistant strains, potentially improving treatment outcomes and accelerating culture conversion.

Citations

Synthetic approaches to potent heterocyclic inhibitors of tuberculosis: A decade review

Heterocyclic inhibitors show promising activity against diverse tuberculosis strains, offering potential for effective antitubercular treatments.

TFA-mediated synthesis of functionalized pyrano[2,3-c]pyrazoles from pyrazol-3-ones, active carbonyl compounds and tert-BuOH

TFA-mediated synthesis of functionalized pyrano[2,3-c]pyrazoles from pyrazol-3-ones, active carbonyl compounds, and tert-BuOH enables the synthesis of LUMOdiene-controlled inverse [4 + 2] cycload

Strategies towards the synthesis of anti-tuberculosis drugs.

Semisynthetic approaches and asymmetric synthesis are effective strategies for synthesizing anti-tuberculosis drugs, particularly for aminoglycoside antibiotics.

Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted N-(2-alkynylphenyl)acetamides.

Organic amines (TNPA and DIEA) effectively synthesize 3-halogeno-substituted 4-benzoylquinolin-2-(1H)-ones from N-(2-alkynylphenyl)-substituted trihaloacetamides

An Organocatalytic Novel Synthesis of Polyfunctionalized Bis‐2,5‐dihydrofuran‐3‐carboxylates via Domino‐MCR Strategy

This novel organocatalytic method allows for the efficient and sustainable synthesis of diverse substituted bis-2,5-dihydrofuran-3-carboxylates at ambient temperature, with no hazardous reagents or solvents needed.

Palladium-catalyzed domino sequence for the synthesis of N-aryl quinolinone-3-carboxylate derivatives and their anti-proliferative activity

The developed Palladium-catalyzed domino reaction efficiently synthesized N-aryl quinolinone-3-carboxylate derivatives with good to moderate anti-proliferative activity, particularly against MCF-7 and KB cancer cell lines.

Cobalt salt-catalyzed carbocyclization reactions of α-bromo-N-phenylacetamide derivatives.

This study developed an efficient and low-cost method for the synthesis of 4-substituted quinolin-2-(1H)-ones using cobalt salt-catalyzed carbocyclization reactions of arylethenyl substituted -bromo-N-phenylace

Manganese(III) acetate mediated oxidative radical cyclizations of α-substituted N-[2-(phenylethynyl)phenyl]acetamides

Manganese(III) acetate effectively synthesizes 3,4-disubstituted quinolin-2(1 H)-ones from -substituted N-[2-(phenylethynyl)phenyl]acetamides, with various functional

Novel synthesis and cytotoxic activity of 1,4-disubstituted 3-methylidene-3,4-dihydroquinolin-2(1H)-ones

This study developed a novel synthesis method for 1,4-disubstituted 3-methylidene-3,4-dihydrodihydroquinolin-2(1H)-ones, which showed promising cytotoxic activity.