Friedländer synthesis of polysubstituted quinolines and naphthyridines promoted by propylphosphonic anhydride (T3P®) under mild conditions

Jida, Mouhamad; Deprez, Benoı̂t

doi:10.1039/c2nj21043f

Cited by 32 publications

(17 citation statements)

References 42 publications

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“…Yield: 384 mg (92%); colorless crystals; mp 141-142 °C (Lit. 42 133-135 °C). 39, 155.57, 146.16, 146.13, 134.82, 132.61, 132.20, 131.22 (2×) Single-crystal X-ray crystallography: A crystal of 1ab was grown by slow diffusion of EtOAc into a solution of 1ab in CH 2 Cl 2 to yield colorless prisms.…”

Section: Ethyl 6-chloro-2-(4-methoxyphenyl)-4-phenylquinoline-3-carbomentioning

confidence: 99%

“…Yield: 316 mg (92%); colorless crystals; mp 184-185 °C (Lit. 42 181-183 °C). 25, 148.99, 146.43, 142.90, 134.17, 132.06, 131.99, 131.18, 130.19, 129.12 (2×), 128.97 (2×), 128.84, 127.77, 125.71, 124.91, 123.66, 123.17, 122.55, 117.19, 66.61 Single-crystal X-ray crystallography: A crystal of 6n was grown by slow diffusion of EtOAc into a solution of 6n in CH 2 Cl 2 to yield colorless prisms.…”

Section: -Chloro-7-phenyl-6h-chromeno[43-b]quinoline (6n) 42mentioning

confidence: 99%

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Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Chan¹,

Lai²,

Wang³

2020

Synthesis

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An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired quinolines in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction analysis.

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Section: Ethyl 6-chloro-2-(4-methoxyphenyl)-4-phenylquinoline-3-carbomentioning

confidence: 99%

Section: -Chloro-7-phenyl-6h-chromeno[43-b]quinoline (6n) 42mentioning

confidence: 99%

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Chan¹,

Lai²,

Wang³

2020

Synthesis

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“…47 Besides, Jida and Deprez demonstrated the high yield and great versatility of a similar synthesis using T3P ® as a stoichiometric catalyst, at mild temperatures (60ºC) and short reactions times (30-60 minutes). 48 This method presents great environmental features through the high yield obtained, the use of easily obtainable reagents and environmental friendly catalysts. Nevertheless, the high costs of T3P ® may be inconvenient in comparison with other methods described.…”

Section: Scheme 7 B) Mild Temperaturesmentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

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The quinoline scaffold is present in a vast number of natural compounds and pharmacologically active substances, comprising a significant segment of the pharmaceutical market. The classical methods for the synthesis of this heterocyclic skeleton require the use of expensive starting materials and high temperature conditions. Chemists play a fundamental role in the construction of a sustainable future through the pursuit of greener chemical processes. As so, the development of new synthetic methods using more efficient energy sources and less hazardous solvents as well as renewable and eco-friendly catalysts to attain the quinoline scaffold can provide significant environmental and economic advantages. This review unveils green methods used in the synthesis of quinolones. Important green metrics are calculated for each proposed method and the statistical analysis allowed us to propose the best approaches for further investigation. The applied research is eventually unveiling the full potential of Friedländer and/or multicomponent reactions, to improve atom economy. The quinoline structural motif is readily available through a number of classical synthetic routes and from commercially available reagents. The Friedländer synthetic method (A) from ortho-aminoacetophenones (10) and the Skraup (B), Combes (D) and Doebner-Miller (F) syntheses from anilines (11), as well as its adaptations, are good examples. Moreover, the Conrad-Limpach (C), Gould-Jacobs (E) and Camps (G) routes for the synthesis of quinolones are widely used methods (Scheme 1). Still, all classical methods have similar disadvantages, requiring highly acidic and/or oxidizing media, high temperatures and long reaction times.Moreover, most of these synthetic routes present selectivity problems with meta-substituted substrates and its versatility is limited by the reactivity of the methylenic carbon involved in the aldol reaction. 19 Although efficient and versatile, classical routes towards the synthesis of quinolines present serious environmental concerns as most synthetic routes use great excess of a reagents and produce a significant amount of toxic waste.

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“…23 The advantages of T3P have been utilized in organic synthesis not only as coupling reagent but also as dehydrating agent and for various functional group interconversions that is, for the synthesis of nitriles, isonitriles, oxadiazoles, and thiadiazoles. 24 Recently, T3P has been used as catalyst for the preparation of polysubstituted quinolines 25 and for the synthesis of fused heterocycles. 26 28 The same reaction conditions failed to give good yield of 2a (Table 1, entry 1) in 30 min.…”

Section: T R a C Tmentioning

confidence: 99%

Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU

Sharnabai

Nagendra

Vishwanatha

et al. 2013

Tetrahedron Letters

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Friedländer synthesis of polysubstituted quinolines and naphthyridines promoted by propylphosphonic anhydride (T3P®) under mild conditions

Cited by 32 publications

References 42 publications

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Synthesis of Quinolines: A Green Perspective

Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU

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