Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines

Tewari, Neetu; Dwivedi, Namrata; Tripathi, Rama Pati

doi:10.1016/j.tetlet.2004.10.057

Cited by 139 publications

(58 citation statements)

References 19 publications

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“…However, this method has several disadvantages including longer reaction times, the us of an excess amount of organic solvent, lower product yields and harsh refluxing conditions. Since the method of Hantzsch was described more than a use century ago [17][18][19] , several efficient methods have been developed for the synthesis of 1, 4-dihydropyridines that involve the use of a microwave [20][21][22] , ionic liquids [23][24] , high temperatures in refluxing solvent [25][26][27][28][29][30][31][32][33][34][35] , TMSCl-NaI 36 and metal triflates 37 . However, the use of high temperatures, expensive metal precursors and the resultant longer reaction times limit these methods.…”

Section: Introductionmentioning

confidence: 99%

Al2(SO4)3 IS AN EFFICIENT AND MILD ACID CATALYST FOR THE ONE-POT, FOUR-COMPONENT SYNTHESIS OF POLYHYDROQUINOLINE

Kulkarni¹

2014

J. Chil. Chem. Soc.

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Aluminium sulfate has mild acidity, yet the acidity of aluminium sulfate is not taken advantage of in organic synthesis. Here, we utilized aluminium sulfate for the first time in a multicomponent reaction for the synthesis of polyhydroquinoline. A four-component one-pot synthesis of polyhydroquinoline was carried out by condensing dimedone, aromatic aldehyde, ethyl acetoacetate, and ammonium acetate using a catalytic amount of aluminium sulfate (10%) refluxed in ethanol. The present protocol using aluminium sulfate a mild solid catalyst has several merits, such as low cost, high yield, and shorter reaction time, with no byproducts.

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Section: Introductionmentioning

confidence: 99%

Al2(SO4)3 IS AN EFFICIENT AND MILD ACID CATALYST FOR THE ONE-POT, FOUR-COMPONENT SYNTHESIS OF POLYHYDROQUINOLINE

Kulkarni¹

2014

J. Chil. Chem. Soc.

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“…Some of the synthetic methods are use of microwave irradiation technique [25,26], refluxing at high temperature [27][28][29][30][31], use of ionic liquid [32], use of catalysts like SiO 2 /HClO 4 [33], SiO 2 /NaHSO 4 [34], I [35], bakers' yeast [36], metal triflates [37], tetrabutylammonium hydrogen sulfate [38], organocatalysts [39], PTSA [40], iron trifluoroacetate [41], TMSCl [42] and Ni nanoparticles [43].…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Fast Synthesis of CuO Nanoflakes: Catalytic Application in the Synthesis of 1,4-Dihydropyridine

Bajaj¹,

Tekade²,

Lakhotiya³

et al. 2017

Acta Phys. Pol. A

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CuO nanoflakes were successfully synthesized by microwave irradiation, using copper(II) sulphate and sodium hydroxide (NaOH) as the starting materials and ethanol as the solvent. The CuO nanoflakes were characterized by using techniques such as X-ray powder diffraction, field emission scanning electron microscopy, and UV-visible absorption spectroscopy, Fourier transform infra-red spectroscopy. The synthesized CuO nanoflakes were found to have morphology like nanoflakes with narrow size distribution and high purity. Moreover, the synthesized CuO nanoflakes were used as an efficient catalyst for synthesis of a series of dihydropyridine derivatives. Optimization studies with different catalysts and solvents reveal that CuO nanoparticle in the water/ethanol mixture is efficient catalyst/solvent system for the synthesis of dihydropyridine derivative.

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“…However, the yield of 1,4-DHP obtained by Hantzsch method is generally low [13][14][15]. Various methods for the synthesis of dihydropyridine derivatives are described in the literature including condensation of aromatic aldehydes, β-dicarbonyl compounds and ammonium acetate using of microwave [16], ionic liquids [17], tetrabutylammonium hydrogen sulfate [18], silica gel/NaHSO 4 [19], AlCl 3 .6H 2 O [20], TMSI [21], triphenylphosphine [22], InCl 3 [23], I 2 [24], cellulose sulfuric acid [25], alumina sulfuric acid [26], SiO 2 /HClO 4 [27], metal triflate [28], Fe(CF 3 CO 2 ) 3 [29], nano CuO [30], nano MgO [31], ultrasound irradiation [32], solvent free [33], and aqueous media [34].…”

Section: Introductionmentioning

confidence: 99%

A simple and efficient approach for synthesis of 1,4-dihydro-pyridines using nano-crystalline solid acid catalyst

Teimouri

Ghorbanian²,

Moatari³

2013

Bull. Chem. Soc. Eth.

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ABSTRACT. A simple highly versatile and efficient synthesis of various 1,4-dihydropyridines in the condensation of aromatic aldehydes with β-dicarbonyl compounds and ammonium acetate in the presence of nano-sulfated zirconia, nano-structured ZnO, nano-γ-alumina and nano-ZSM-5 zeolites, as catalyst in the ethanol at moderate temperature is presented. The advantages of method are short reaction times and milder conditions and easy work-up. The catalysts can be recovered for the subsequent reactions and reused without any appreciable loss of efficiency.

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Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines

Cited by 139 publications

References 19 publications

Al2(SO4)3 IS AN EFFICIENT AND MILD ACID CATALYST FOR THE ONE-POT, FOUR-COMPONENT SYNTHESIS OF POLYHYDROQUINOLINE

Al2(SO4)3 IS AN EFFICIENT AND MILD ACID CATALYST FOR THE ONE-POT, FOUR-COMPONENT SYNTHESIS OF POLYHYDROQUINOLINE

Microwave Assisted Fast Synthesis of CuO Nanoflakes: Catalytic Application in the Synthesis of 1,4-Dihydropyridine

A simple and efficient approach for synthesis of 1,4-dihydro-pyridines using nano-crystalline solid acid catalyst

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