Metal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl 4,4-difluorobut-2-ynoate with 2-aminobenzonitriles

Fan, Zhenhua; Yang, Shaolin; Xin, Peng; Zhang, Cheng; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo

doi:10.1016/j.tet.2019.01.001

Cited by 8 publications

(4 citation statements)

References 44 publications

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“…Cao et al [65] described aD BU-promoted cascade Michael addition/cyclization of methyl 4,4-difluorobut-2-ynoate with 2aminobenzonitriles to generate 2-difluoromethylated quinolines. Thisa pproach applies readily available 4,4-difluorobut-2ynoate as the fluorinated building block (Scheme 47).…”

Section: Synthesis Of 2-fluoroalkylatedmentioning

confidence: 99%

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Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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As one of the most widely investigated compound skeleton, quinolines possess important medicinal and biological activities. As such, ag reat number of literatures, including reviews, have reported various methodologies to construct quinolines. Recently,o rganocatalyzed reactions have attracted the attention of organic chemists due to its being "green" because the reactions avoid the use of toxic metals.I nt his review, various distinctive contributionsa re surveyed with specific emphasis on organocatalyzed reactions for quinoline core constructions.

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Section: Synthesis Of 2-fluoroalkylatedmentioning

confidence: 99%

“…Cao et al . described a DBU‐promoted cascade Michael addition/cyclization of methyl 4,4‐difluorobut‐2‐ynoate with 2‐aminobenzonitriles to generate 2‐difluoromethylated quinolines.…”

Section: Synthesis Routes To Functionalized Quinolinesmentioning

confidence: 99%

Organocatalyzed Synthesis of Functionalized Quinolines

Niu

Liang

2019

Chemistry An Asian Journal

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“…No doubt a diverse range of synthetic protocols including both catalytic and noncatalytic have been developed for construction of new compounds with virtually boundless combinations of functionality having quinoline and 8-hydroxy quinoline scaffold. [8,[65][66][67][68][69][70][71][72] L-proline as catalyst was reported for the synthesis of quinoline derivatives from anilines but reaction time was 8 to 12 hours [66] so we use ammonium acetate as catalyst in one-pot protocol which reduced the reaction time to 20 to 120 minutes. Ammonium acetate is used as catalyst as well as reagent in synthesis of a wide range of heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

Tabassum

Ashfaq

Oku

2020

Journal of Heterocyclic Chem

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A one‐pot quick and efficient multicomponent reaction has been developed for the synthesis of a new series of functionalized 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives using 30 mol% ammonium acetate in ethanol as solvent. This economical protocol run smoothly to give variety of quinoline derivatives in 55% to 98% yield from inexpensive reagents and catalyst in mild reaction conditions. Various spectroscopic techniques like FTIR, 1 H NMR and 13 C NMR, MALDI‐TOF‐MS, and EI‐MS were used to study and confirm their structure.

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“…Owing to their vital role in medicinal agents and natural products, quinolines have become important synthetic targets for chemists. A diverse range of one pot multicomponent protocols including both catalytic and non-catalytic synthetic methods have been developed that use diverse starting materials to construct the quinoline ring with virtually boundless combinations of functionality [ 10 , 57 , 58 , 59 , 60 , 61 , 62 , 63 ]. L-proline as catalyst was reported for the synthesis of 4-phenyl quinoline derivatives from anilines but reaction time was 8–12h [ 58 ] so we use ammonium acetate as catalyst in one pot protocol which reduced the reaction time to 20min- 90min.…”

Section: Introductionmentioning

confidence: 99%

7-Hydroxy-4-phenyl-1, 2-dihydroquinoline derivatives: synthesis via one-pot, three-component reaction and structure elucidation

Tabassum

Ashfaq

Oku

2020

Heliyon

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We have developed a new and facile one pot three component protocol catalyzed by ammonium acetate for construction of new functionalized 7-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives. A variety of quinoline derivatives were obtained in good to excellent yield from inexpensive reagents and catalyst in mild reaction conditions that provide atom economy and cost efficacy. Various spectroscopic techniques like FTIR, 1 HNMR and 13 CNMR were employed to study their structure while mass of the synthesized compounds were confirmed through MALDI-TOF-MS and EI mass spectrometry.

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Metal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl 4,4-difluorobut-2-ynoate with 2-aminobenzonitriles

Cited by 8 publications

References 44 publications

Organocatalyzed Synthesis of Functionalized Quinolines

Organocatalyzed Synthesis of Functionalized Quinolines

Development of an efficient, one‐pot, multicomponent protocol for synthesis of 8‐hydroxy‐4‐phenyl‐1,2‐dihydroquinoline derivatives

7-Hydroxy-4-phenyl-1, 2-dihydroquinoline derivatives: synthesis via one-pot, three-component reaction and structure elucidation

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