A green approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (and -thiones) using N,N-diethyl-N-sulfoethanaminium hydrogen sulfate

Zare, Abdolkarim; Nasouri, Zahra

doi:10.1016/j.molliq.2016.01.056

Cited by 32 publications

(14 citation statements)

References 41 publications

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“…[TEASA][TFA] as a viscous pale yellow liquid. The spectroscopic data of [TEASA][TFA] include: IR (nujol, cm −1 ): 852, 1068, 1172, 1229, 1291, 1709, 2400-3600; 1 H NMR (400 MHz, DMSO-d6): δ (ppm) 1.21 (t, J = 7.5 Hz, 9H), 3.10 (q, J = 7.5 Hz, 6H), 10.00 (br., 1H); 13 C NMR (100 MHz, DMSO-d6): δ (ppm) 8.7, 46.3, 115.4 (q), 158.8 (q); MS: m/z 295 (M + ), 296 (M + +1).These spectral data are in accordance with the literature[8,9].…”

supporting

confidence: 85%

“…In continuation of our previous studies on the production of acidic ionic-liquid catalysts in which a SO3H group bonded to a tertiary amine or heterocyclic nitrogen [7][8][9][10], we prepared a novel member of this attractive class of ionic liquids namely triethylaminium-Nsulfonic acid trifluoroacetate {[TEASA][TFA]}, according to Scheme 1.…”

Section: Production and Characterization Of The Catalystmentioning

confidence: 99%

“…salts) which melt at or below 100 °C. These salts have attracted rising interest in the last decade, due to their unique properties, such as: high thermal and chemical stability, non-flammability, non-volatility, wide liquid-state temperature range, large electrochemical window, favorable salvation behavior, and ability to use as solvent, reagent and catalyst in organic synthesis [1][2][3][4][5][6][7][8][9][10]. Among the different kinds of ionic liquids, Brønsted acidic ones have been designed to replace solid acids and traditional mineral liquid acids to catalyze chemical transformations [3][4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

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Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

Saadat¹,

Zare²,

Jamadi³

et al. 2017

Bull. Chem. React. Eng. Catal.

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In this work, a novel Brønsted acidic ionic liquid namely triethylaminium-N-sulfonic acid trifluoroacetate {[TEASA][TFA]} has been synthesized by the reaction of NEt3 with ClSO3H, and then with CF3CO2H. The ionic liquid has been characterized by studying its spectroscopic data (1H and 13C NMR, FT-IR, and mass spectra). Afterward, it has been utilized as a highly effective and general catalyst to promote the following organic reactions in solvent-free conditions: (i) the production of 1-thioamidoalkyl-2-naphthols from arylaldehydes, 2-naphthol and thioacetamide, and (ii) the preparation of 14-aryl-14H-dibenzo[a,j]xanthenes from arylaldehydes and 2-naphthol. It is noteworthy that [TEASA][TFA] has catalyzed the reactions under milder conditions relative to most of the reported methods. Moreover, it afforded the both products in higher yields with respect to most of the previous works. Copyright © 2018 BCREC Group. All rights reservedReceived: 21st June 2017; Revised: 6th October 2017; Accepted: 9th October 2017; Available online: 11st June 2018; Published regularly: 1st August 2018How to Cite: Saadat, A., Zare, A., Jamadi, F., Abdolalipour-Saretoli, M. (2018). Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions. Bulletin of Chemical Reaction Engineering & Catalysis, 13 (2): 204-212 (doi:10.9767/bcrec.13.2.1280.204-212)

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supporting

confidence: 85%

Section: Production and Characterization Of The Catalystmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

Saadat¹,

Zare²,

Jamadi³

et al. 2017

Bull. Chem. React. Eng. Catal.

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“…Therefore, we decided to explore the feasibility of alkylated DHPMs. Thus, this investigation had allowed us to describe a new efficient method for the preparation of new compounds with regioselective N1-alkylation and N1/N3-bis-alkylation of DHPMs analogues (Mohamadpour et al, 2016;Zare & Nasouri 2016).…”

Section: Structure Descriptionmentioning

confidence: 99%

5-Acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-1-(prop-2-ynyl)-3,4-dihydropyrimidin-2(1H)-one

Kaoukabi¹,

Taourirte²,

Azhari³

et al. 2017

IUCr Data

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In the title compound, C18H20N2O4, the 3,4-dihydropyrimidin-2(1H)-one ring has a screw-boat conformation. The mean plane through this heterocycle is almost perpendicular to the prop-2-ynyl chain and to the benzene ring, with which it makes a dihedral angle of 87.63 (6)°. The plane through the acetyl group makes a dihedral angle of 33.11 (8)° with the mean plane of the heterocycle. There is an intramolecular C—H...O hydrogen bond present forming anS(6) ring motif. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming layers parallel to thebcplane. There are also C—H...π interactions present within the layers.

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“…Currently, heterogenization of ionic liquids (ILs) via immobilization on solid supports (i. e. synthesis of organic‐inorganic hybrid materials), and their application as catalysts in organic synthesis have attracted much attention, because solid‐supported ILs have simultaneously the advantages of ionic liquids and heterogeneous catalysts . The particular properties of ILs include non‐flammability, suitable thermal, chemical and electrochemical stability, easy preparation and functionalization, enhanced reactivity as well as effectiveness, non‐volatility, green nature, recyclability, and ability to catalyze a wide range of organic transformations ,. The advantages of heterogeneous catalysts consist of easy usage, simple isolation and recyclability, high stability, straightforward workup of reaction mixture, eco‐friendly reaction conditions, and capability to catalyze various organic reactions ,…”

Section: Introductionmentioning

confidence: 99%

A Nanostructured Organic‐Inorganic Hybrid Material: Preparation, Characterization and Catalytic Performance for the Synthesis of N,N′‐Alkylidene Bisamides

Zare

Khanivar

Irannejad‐Gheshlaghchaei

et al. 2019

ChemistrySelect

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In this research, a novel nanostructured mesoporous organicinorganic hybrid material, based on dicationic ionic liquidanchored with silica, namely nano-2-[N',N'-dimethyl-N'-(silica-npropyl)ethanaminium chloride]-N,N-dimethylaminium bisulfate {nano-[DSPECDA][HSO 4 ]} has been prepared, and characterized by FT-IR, energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FE-SEM), X-ray diffraction (XRD), thermal gravimetry (TG), differential thermal gravimetric (DTG), differential thermal analysis (DTA), and adsorption/desorption porosimetry (BET, Langmuir, adsorption/ desorption isotherm, BJH, and t-plot) methods. Thereafter, the nanomaterial has been utilized as a highly effectual, heterogeneous and recyclable nanocatalyst for the synthesis of N,N'alkylidene bisamides via the condensation reaction of arylaldehydes (1 eq.) with primary amides (2 eq.) under solvent-free conditions. The reaction results were better compared with the literature in terms of two or more of these factors: turnover frequency (TOF), yield, temperature, time, and the reaction media. Moreover, a plausible mechanism for the synthesis has been proposed.

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A green approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (and -thiones) using N,N-diethyl-N-sulfoethanaminium hydrogen sulfate

Cited by 32 publications

References 41 publications

Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

Highly Efficient Synthesis of 1-Thioamidoalkyl-2-naphthols and 14-Aryl-14H-dibenzo[a,j]xanthenes using a Novel Ionic Liquid: Catalyst Preparation, Characterization and Performing the Reactions

5-Acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-1-(prop-2-ynyl)-3,4-dihydropyrimidin-2(1H)-one

A Nanostructured Organic‐Inorganic Hybrid Material: Preparation, Characterization and Catalytic Performance for the Synthesis of N,N′‐Alkylidene Bisamides

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