One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols

Heydari, Akbar; Khaksar, Samad; Tajbakhsh, Mahmood; Bijanzadeh, Hamid Reza

doi:10.1016/j.jfluchem.2009.03.014

Cited by 103 publications

(44 citation statements)

References 47 publications

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“…Heydari, et al 58 has synthesized 1,4-dihydropyridines 123a, 123b, 123d, 123e, 123h, 123j, 123l, 144m and 145a-b in excellent yields by the reaction of aldehydes, alkyl acetoacetate 110a-b, and ammonium acetate (Scheme 49) at 70 C in triuoroethanol (TFE). The advantage of this reaction was the solvent (TFE), which can be readily separated from reaction products and recovered in excellent purity for reuse.…”

Section: Scheme 44mentioning

confidence: 99%

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

2017

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Dihydropyridine (DHP) is among the most beneficial scaffolds that have revolutionised pharmaceutical research with unprecedented biological properties. Over the years, metamorphosis of easily accessible 1,2-and 1,4-dihydropyridine (1,4-DHP) intermediates by synthetic chemists has generated several drug molecules and natural products such as alkaloids. The 1,4-dihydropyridine (1,4-DHP) moiety itself is the main fulcrum of several approved drugs. The present review aims to collate the literature of 1,2-and the 1,4-DHPs relevant to synthetic and medicinal chemists. We will describe various methodologies that have been used for the synthesis of this class of compounds, including the strategies which can furnish enantiopure DHPs, either by asymmetric synthesis or by chiral resolution.We will also elaborate the significance of DHPs towards the synthesis of natural products of medicinal merit.

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Section: Scheme 44mentioning

confidence: 99%

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

2017

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“…[31,32] Furthermore, polyhydroquinoline derivatives are well-known as Ca 2+ channel blockers and drugs of NADH co-enzymes. [33,34] The biological and pharmaceutical activities of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives have encouraged organic chemists to develop numerous one-pot, green strategies for their preparation. In recent times, search for finding new SCHEME and efficient synthetic routs toward the preparation of 2, 3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives have been focused on using highly active and reusable catalysts under environmentally benign mediums.…”

Section: Introductionmentioning

confidence: 99%

Magnetic Fe3O4 nanoparticles supported imine/Thiophene‐nickel (II) complex: A new and highly active heterogeneous catalyst for the synthesis of polyhydroquinolines and 2, 3‐dihydroquinazoline‐4(1H)‐ones

Shiri

Heidari

Kazemi

2017

Applied Organom Chemis

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A new magnetically separable nickel catalyst (Ni(NO 3 ) 2− Imine/ThiopheneFe 3 O 4 @SiO 2 ) was readily prepared and structurally characterized by Fourier transform infrared spectroscopy (FT-IR), Scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), Vibrating sample magnetometer (VSM), X-Ray diffraction (XRD) and Atomic absorption spectroscopy (AAS).The Ni(NO 3 ) 2− Imine/Thiophene-Fe 3 O 4 @SiO 2 exhibited efficient catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones and polyhydroquinolines.Catalysis research under water and solvent-free conditions makes also this synthetic protocol ideal and fascinating from the environmental point of view. The catalyst can be magnetically recovered after the reaction and can be reused for many times without appreciable decrease in activity.

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“…Recently, due to the varied pharmaceutical and biological applications connected to the polyhydroquinolines structural motif, a huge attention has been paid to the production of these versatile organic compounds. Substituted 1,4-dihydropyridines are renowned as calcium channel modulators and they can be applied as a treatment for the therapy of the cardiovascular diseases [18].…”

Section: Introductionmentioning

confidence: 99%

Novel magnetic nanoparticles with ionic liquid tags as a reusable catalyst in the synthesis of polyhydroquinolines

et al. 2016

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In this paper, we have introduced {Fe3O4@SiO2@(CH2)3Im}C(NO2)3 as a novel and heterogeneous reusable catalyst for the four component preparation of the polyhydroquinoline derivatives under mild and eco-friendly reaction conditions. The structural confirmation of the novel heterogeneous reusable promoter was fully made using appropriate technical skills such as FT-IR, X-ray diffraction patterns (XRD), Field emission scanning electron microscopy (FESEM), Energy-dispersive spectroscopy (EDS) elemental mapping analysis, High Resolution transmission electron microscopy (HRTEM), thermogravimetry (TG), derivative thermal gravimetric (DTG), differential thermal (DTA) and vibrating sample magnetometer (VSM) analysis. The presented nano magnetic heterogeneous catalyst was successfully applied for the synthesis of the polyhydroquinoline derivatives via a four component condensation of a good range arylaldehydes, dimedone, ethyl acetoacetate or methyl acetoacetate as β-ketoester, and ammonium acetate as nitrogen source under solvent free conditions. Also, the experimental evidence has demonstrated that the {Fe3O4@SiO2@(CH2)3Im}C(NO2)3 could act as a nano magnetically recoverable and reusable catalyst without any meaningful drop in the yield and the reaction time at least for eight times.

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One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols

Cited by 103 publications

References 47 publications

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

Magnetic Fe3O4 nanoparticles supported imine/Thiophene‐nickel (II) complex: A new and highly active heterogeneous catalyst for the synthesis of polyhydroquinolines and 2, 3‐dihydroquinazoline‐4(1H)‐ones

Novel magnetic nanoparticles with ionic liquid tags as a reusable catalyst in the synthesis of polyhydroquinolines

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