The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

Buu‐Hoï, Ng. Ph.; Royer, R.; Xuong, Ng. D.; Jacquignon, P.

doi:10.1021/jo50015a019

Cited by 60 publications

(19 citation statements)

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“…9−13 Given the importance of the quinoline scaffold in the fields of both pharmaceutical and organic chemistry, synthesis of quinoline derivatives has received tremendous attention since Skraup first reported the classical synthetic method of quinoline in 1880. 14 Over the past few decades, numerous methods based on various mechanisms, including Conrad−Limpach−Knorr, 15 Friedlander, 16 Doebner−von Miller, 17 Pfitzinger, 18 or Combes, 19 have been developed for the preparation of substituted quinolones. However, multiple synthetic steps and harsh reaction conditions, such as high temperatures, strong base, acid or metal catalysts, still limit the applications of these strategies.…”

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confidence: 99%

Highly Selective and Efficient Synthesis of 7-Aminoquinolines and Their Applications as Golgi-Localized Probes

Chen

Liu

et al. 2019

ACS Med. Chem. Lett.

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Quinoline derivatives have extensively been used for both pharmaceutical agents and bioimaging. However, typical synthesis of quinoline derivatives is generally through strong acid/base-catalyzed or metal-catalyzed methods at high temperatures. Here we report a catalyst-free synthesis of 2,4-disubstituted 7-aminoquinolines with high selectivity and good yields via the introduction of a trifluoromethyl group. It is discovered that quinolines containing both amino and trifluoromethyl groups exhibit strong intramolecular charge-transfer fluorescence with large Stokes shifts. We further applied the obtained quinolines to live-cell imaging and found that some of the derivatives can target specifically Golgi apparatus in various cell lines (HeLa, U2OS, and 4T1 cells) in vitro and the colocalization with commercial Golgi marker is retained during the mitosis in HeLa cells. Moreover, the quinoline dyes can also be used for Golgi apparatus imaging with two-photon fluorescence microscopy. These results provide new insights into developing low cost Golgi-localized probes.

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confidence: 99%

Highly Selective and Efficient Synthesis of 7-Aminoquinolines and Their Applications as Golgi-Localized Probes

Chen

Liu

et al. 2019

ACS Med. Chem. Lett.

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“…In many cases, reactions that normally require many hours at reflux temperature under normal conditions can be completed within several minutes or even seconds in a microwave oven, even at comparable reaction temperatures . Quinoline synthesis has received much focus, and many methods have been developed for the synthesis, such as Skraup, Doebner‐Miller, Pfitzinger, and Friedlander . Among all the methods, Friedlander annulation is one of the most popular methods for the substituted quinoline synthesis .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel quinoline‐thiosemicarbazide hybrids and evaluation of their biological activities, molecular docking, molecular dynamics, pharmacophore model studies, and ADME‐Tox properties

Patel

Darji

Patel

et al. 2020

Journal of Heterocyclic Chem

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In the present study, a novel series of N‐((substituted)carbamothioyl)‐2,4‐dimethylquinoline‐3‐carboxamide (7a‐7s) was synthesized by microwave‐assisted method. Structure of these derivatives was examined by spectroscopic techniques such as 1H NMR, 13C NMR, FT‐IR, and ESI‐MS. Further, the novel synthesized compounds were evaluated for their in‐vitro biological activities against antibacterial, antifungal, antimalarial, and antituberculosis activity as well as for in‐silico study. The antimalarial results demonstrated that compounds 7c and 7q (0.02 μg/mL) have notable potency against Plasmodium falciparum compared with chloroquine (0.02 μg/mL); compounds 7l (0.10 μg/mL), 7e, 7s (0.19 μg/mL), 7b, 7p (0.15 μg/mL), 7a, 7f, and 7f (0.25 μg/mL) also exhibited good activity against P. falciparum compared with quinine (0.26 μg/mL) as standard drug. Docking was performed on PFDHFR‐TS, given the effect of compounds against the P. falciparum strain was excellent in comparison with standard drug. Molecular docking suggested that compounds 7b, 7i and 7c, 7e, and 7l closely bind with the active site of protein 3JSU and 4DP3, respectively, and compared with biological activity. We have also carried out molecular dynamics simulation on the best dock compound 7e complex with PDB: 3JSU to check the stability of docked complex and their molecular interaction. The calculated ADME‐Tox descriptors for the synthesized compounds validated good pharmacokinetics properties, suggesting that these compounds could be used as hit for the development of the new active agents.

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“…The above‐mentioned reactions suffer from several drawbacks like harsh reaction conditions, high temperature, and volatile organic solvents and consist of many multiple steps. Skraup‐Doebner‐Von Miller, Pfitzinger‐Borsche, and Esmaeilpoura and Javidi reported many synthetic routes. The synthesis which involves the condensation of o ‐haloacetophenones with urea or primary amines, requires high temperature and long reaction time (150°C, 48 hours).…”

Section: Introductionmentioning

confidence: 99%

An environmentally benign, green, and efficient ionic liquid catalyzed synthesis of Quinoline derivatives via Knoevenagel condensation

Syed

Asiri²

2019

Journal of Heterocyclic Chem

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The present investigation is in the interest of one-pot, environmentally friendly and efficient protocol for the synthesis of quinoline derivatives from 2-aminoarylketones and active methylene compounds in the presence of L-proline and ionic liquid 1,3-dimethylimidazolium methyl sulfate [MMIm] [MSO 4 ]. The Ionic liquid which is used as a catalyst can be reused several times. The results obtained by using [MMIm][MSO 4 ] were also compared with those described in the literature. The advantages of the method are shorter reaction time, milder conditions, easy workup and better yields. The catalyst [MMIm][MSO 4 ] can be recovered for the subsequent reactions and reused without any appreciable loss of efficiency. This method of synthesis widens the applicability of Ionic liquids in heterocyclic compounds.

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The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

Cited by 60 publications

References 0 publications

Highly Selective and Efficient Synthesis of 7-Aminoquinolines and Their Applications as Golgi-Localized Probes

Highly Selective and Efficient Synthesis of 7-Aminoquinolines and Their Applications as Golgi-Localized Probes

Synthesis of novel quinoline‐thiosemicarbazide hybrids and evaluation of their biological activities, molecular docking, molecular dynamics, pharmacophore model studies, and ADME‐Tox properties

An environmentally benign, green, and efficient ionic liquid catalyzed synthesis of Quinoline derivatives via Knoevenagel condensation

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