One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[<i>b</i>]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

Sayahi, Mohammad Hosein; Gholami, Maryam; Meheiseni, Melan; Sayyahi, Soheil

doi:10.1515/znb-2019-0155

Cited by 16 publications

(6 citation statements)

References 34 publications

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“…Sayahi et al [ 65 ] devised an efficient method for the preparation of DES for pyran derivatives (Scheme 20, Method 1). The eutectic mixture worked as both the acidic catalyst and solvent for conversion.…”

Section: Different Synthetic Methodologies For Substituted Pyran Deri...mentioning

confidence: 99%

“…High chemical and thermal stability, water-solubility, less-toxic, low vapor pressure, large viscosity, biodegradable, and cost-efficiency are the special properties of DESs. [64] Sayahi et al [65] devised an efficient method for the preparation of DES for pyran derivatives (Scheme 20, Method 1). The eutectic mixture worked as both the acidic catalyst and solvent for conversion.…”

Section: Des Assisted Synthesismentioning

confidence: 99%

See 1 more Smart Citation

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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Substituted pyrans (4H‐Chromenes) are the most significant structural scaffolds in synthetic and medicinal chemistry. They are found in an array of natural products, medicines, and phytochemical compounds, bearing an explicit of pharmacological activities. The structural importance of substituted pyrans has elicited a huge upsurge in the field of synthesis and biology. Different synthetic approaches of 4H‐chromene scaffolds have been discussed systematically to emphasize their significance in the scientific world. The present article summarizes the different synthetic strategies of substituted pyran derivatives via acid‐base catalysis, ionic liquids, nanomaterials, deep eutectic solvents, bio‐based, visible light, metal catalyzed, and so forth developed in the last decade. Moreover, this article will definitely contribute to the scientific world for developing synthetically and biologically important pyran analogs.

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Section: Different Synthetic Methodologies For Substituted Pyran Deri...mentioning

confidence: 99%

Section: Des Assisted Synthesismentioning

confidence: 99%

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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“…In this context, DHPo's as the Milrinone and the Amrinone are drugs with cardiotonic activity successfully used to treat heart failure (Figure 1). [2] In addition, they and their derivatives have also been reported to possess antitumor [3], antibacterial [4] anti-HIV [5], and other biological activities [6][7][8][9]. These results encourage many research groups to search potentially active DHPo's analogs.…”

Section: Introductionmentioning

confidence: 99%

3,4-Dihydro-2(1H)-Pyridones as Building Blocks of Synthetic Relevance

Chalán-Gualán¹,

Castro²,

Oropeza³

et al. 2022

Preprint

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3,4-Dihydro-2(1H)-pyridones (3,4-DHPo) and their derivatives are privileged structures present in natural products, which has been increased its relevance due to its biological activity in front of a broad range of targets, but especially for its importance as synthetic precursors of a variety of compounds with marked biological activity. Taking into account the large number of contributions published over the years regarding this kind of heterocycle, here we presented a current view of 3,4-dihydro-2(1H)-pyridones (3,4-DHPo), which include general aspects such as those related to nomenclature, synthesis, and biological activity; but also highlighting the importance of DHPo as building blocks of other relevance structures.

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“…A suitable method for synthesis of benzopyrans is three-component condensation of malononitrile and dimedone with various aldehydes. This reaction has been investigated in the presence of various catalysts such a Fe 3 O 4 @SiO 2 @NiSB [ 12 ], oxyammonium-based ionic liquid [ 13 ], WEMFSA [ 14 ], [Bmim]Sac [ 15 ], MNPs–PhSO 3 H [ 16 ], NH 2 @SiO 2 @Fe 3 O 4 MNPs [ 17 ], choline chloride-oxalic acid [ 18 ], SCMNPs@PC/VB1-Zn [ 19 ], MMWCNTs-D-(CH 2 )4-SO 3 H [ 20 ] and Chlorophyll [ 21 ]. In this research a practical, simple and inexpensive procedure for the synthesis of tetrahydrobenzo[ b ]pyran derivatives is reported by the reaction of aldehydes, malononitrile and dimedone in the presence of catalytic amount of nano-silica supported 1,5-diazabicyclo[4.3.0]non-5-en (Nano-SiO 2 /DBN).…”

Section: Introductionmentioning

confidence: 99%

Nano-SiO2/DBN: an efficacious and reusable catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran derivatives

et al. 2021

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Background The nano-sized particles enhance the exposed surface area of the active part of the catalyst, thereby increasing the contact between precursors and catalyst considerably. In this study, nano-SiO2/1,5-diazabicyclo[4.3.0]non-5-en was synthesized, characterized and used as a heterogeneous nanocatalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives. Fourier Transform Infrared Spectroscopy, Field Emission Scanning Electron Microscopy, Brunauer–Emmett–Teller plot, Energy Dispersive X-ray Spectroscopy and Thermo Gravimetric Analysis were used to discern nano-SiO2/1,5-diazabicyclo[4.3.0]non-5-en. Results Tetrahydrobenzo[b]pyrans were synthesized by using nano-SiO2/1,5-diazabicyclo[4.3.0]non-5-en via one-pot three-component condensation of malononitrile, aldehydes and dimedone in H2O/EtOH at 60 °C. The results indicate that tetrahydrobenzo[b]pyrans were synthesized in good to high yields and short reaction times. Conclusions The fundamental privileges of this method are short reaction time, plain procedure, recyclability of catalyst and high yields of products.

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One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

Cited by 16 publications

References 34 publications

An overview of recent advances in the catalytic synthesis of substituted pyrans

An overview of recent advances in the catalytic synthesis of substituted pyrans

3,4-Dihydro-2(1H)-Pyridones as Building Blocks of Synthetic Relevance

Nano-SiO2/DBN: an efficacious and reusable catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran derivatives

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