Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction

Ikuma, Yohei; Nakahira, Hiroyuki

doi:10.1016/j.tet.2011.10.015

Cited by 9 publications

(2 citation statements)

References 28 publications

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“… 1 They have been reported to possess diverse pharmacological properties such as anticancer, 2 anti-HCV, 3 anti-inflammatory, 4 and antidiabetic activities. 5 Also, these heterocyclic frameworks can be found in a plethora of biologically active natural compounds. 6 In parallel, sulfides are a class of important compounds, many of which have been found to exhibit unique pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

“…Quinolinones and spiro[4.5]trienones both have been recognized as important heterocyclic skeletons of biologically active molecules . They have been reported to possess diverse pharmacological properties such as anticancer, anti-HCV, anti-inflammatory, and antidiabetic activities . Also, these heterocyclic frameworks can be found in a plethora of biologically active natural compounds .…”

Section: Introductionmentioning

confidence: 99%

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Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Wang

Ouyang

et al. 2021

J. Org. Chem.

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A highly substituent-dependent rearrangement allows for the novel and SOCl 2 -induced divergent synthesis of 3-methylthioquinolin-2-ones and 3-methylthiospiro[4.5]trienones through intramolecular electrophilic cyclization of N -aryl propyamides. DMSO acts as both solvent and sulfur source, and use of DMSO- h 6 / d 6 enables the incorporation of SCH 3 or SCD 3 moieties to the 3-position of the heterocyclic framework. Different para -substituents trigger divergent reaction pathways leading to the formation of quinolin-2-ones for mild substituents and spiro[4,5]trienones for both electron-withdrawing and -donating substituents, respectively. On the basis of both computational and experimental results, a new mechanism has been put forward that accounts for the exclusive spirolization/defluorination process and the surprising substituent effects.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Wang

Ouyang

et al. 2021

J. Org. Chem.

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A Green Approach for 1,2,3‐Triazole‐Fused Quinolinones via Metal‐Free Cascade [3+2] Cycloaddition/C‐N Coupling Reaction

Majeed

Zhou

Liu³

et al. 2022

ChemistrySelect

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A metal-free cascade reaction of 1-(8-halonaphthalen-1-yl)prop-2-yn-1-ones with sodium azide has been developed for the construction of quinolinone fused triazole frameworks. The reaction proceeded smoothly via an intramolecular metal-free version of the azide-alkyne [3 + 2] cycloaddition. A variety of quinolinone fused triazole derivatives were prepared in good to excellent yields under metal-free conditions. The practicality of this metal-free protocol was further evaluated by gram scale synthesis of quinolinone fused triazole derivatives.

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New tetrazoloquinolinyl methoxyphenyl-4-thiazolidinones: synthesis and antihyperglycemic evaluation

et al. 2016

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Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction

Cited by 9 publications

References 28 publications

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

A Green Approach for 1,2,3‐Triazole‐Fused Quinolinones via Metal‐Free Cascade [3+2] Cycloaddition/C‐N Coupling Reaction

New tetrazoloquinolinyl methoxyphenyl-4-thiazolidinones: synthesis and antihyperglycemic evaluation

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