One-Pot Synthesis of 1,4-Dihydropyridines via a Phenylboronic Acid Catalyzed Hantzsch Three-Component Reaction

Debache, Abdelmadjid; Boulcina, Raouf; Belfaitah, Ali; Rhouati, Salah; Carboni, Bertrand

doi:10.1055/s-2008-1032093

Cited by 124 publications

(51 citation statements)

References 13 publications

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“…Dicarbonyl compounds and their analogs are well known in the synthesis of pyridines [161,162]. Owing to the utility of dicarbonyls, Dong et al [163] have developed a new route for the synthesis of highly substituted pyridines 258 via four- …”

Section: Scheme 70mentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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Section: Scheme 70mentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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“…Numerous synthetic methods have been reported for the preparation of 1,4-dihydropyridines under classical or modified conditions [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. However, the low yields, occurrence of several side products, use of stoichimetric amount of reagents, expensive metal precursors, catalysts that are harmful to environment, use of expensive and toxic transition metallic reagents, complicated work-up methods and longer reaction times limit the use of these methods.…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of polyhydropyridine derivatives via Hantzsch four component condensation in water medium: Use of a recyclable Lewis acid [Ce(SO4)2.4H2O] catalyst

Mosaddegh¹,

Hassankhani²

2012

Bull. Chem. Soc. Eth.

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ABSTRACT. An efficient and eco-friendly method for the synthesis of polyhydroquinoline derivatives using Ce(SO4)2.4H2O as mild and heterogeneous Lewis acid catalyst via the Hantzsch reaction in very short reaction time is reported. A mixture of an appropriate aldehyde, dimedone, ethyl acetoacetate and malononitrile in the presence of the Ce(SO4)2.4H2O at reflux conditions in water based media resulted in good to excellent yields of the corresponding products. The catalyst can be used as selective for some aromatic aldehydes in the reaction conditions.

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“…Therefore, numerous promotions, such as using ionic liquids 13,14 , microwaves [15][16][17] , grinding 18 , silica-supported acids 19,20 , L-proline 21 , HY-zeolite 22 , Bu 4 NHSO 4 23 , boronic acids 24,25 , TMSCl-NaI 26 , ceric ammonium nitrate 27,28 , metal triflates 29,30 , p-TSA 31 , and baker's yeast 32,33 have been developed. However, many of these methods still suffer from several limitations, such as unsatisfactory yield, use of environmentally suspected organic solvents, long reaction time, high temperature, and using expensive and non reusable catalysts.…”

Section: Introductionmentioning

confidence: 99%

Vanadatesulfuric Acid-catalyzed Novel and Eco-benign one-pot Synthesis of Polyhydroquinoline Derivatives under Solvent-free Conditions

Nasr‐Esfahani¹,

Abdizadeh²

2012

Orientjchem.

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A novel and green approach for efficient and rapid synthesis of biologically active polyhydroquinoline derivatives via unsymmetric Hantzsch reaction using nanorods Vanadatesulfuric acid (VSA NRs) as a new and recyclable catalyst under solvent-free conditions was reported. The catalyst was characterized by FT-IR, XRD, XRF and TEM analysis. The present method offers several advantages such as simple procedure, short reaction time, high yields, simple workup, reusability of the catalyst and simple purification of the products.

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One-Pot Synthesis of 1,4-Dihydropyridines via a Phenylboronic Acid Catalyzed Hantzsch Three-Component Reaction

Abstract: A simple, inexpensive, and efficient one-pot synthesis of 1,4-dihydropyridine derivatives was achieved in good yields via the three-component reaction of aromatic aldehydes, ethyl acetoacetate, and ammonium acetate using PhB(OH) 2 as catalyst.

Cited by 124 publications

References 13 publications

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

One-pot synthesis of polyhydropyridine derivatives via Hantzsch four component condensation in water medium: Use of a recyclable Lewis acid [Ce(SO<sub>4</sub>)<sub>2</sub>.4H<sub>2</sub>O] catalyst

Vanadatesulfuric Acid-catalyzed Novel and Eco-benign one-pot Synthesis of Polyhydroquinoline Derivatives under Solvent-free Conditions

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