Experimental and theoretical investigation of new furan and thiophene derivatives containing oxazole, isoxazole, or isothiazole subunits

Civcir, Pervin Ünal; Kurtay, Gülbin; Sarikavak, Kübra

doi:10.1007/s11224-016-0863-1

Cited by 17 publications

(13 citation statements)

References 75 publications

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“…5 Good solubility in water and high thermal stability with respect to other heteroaromatic systems make these molecules suitable for the synthesis of therapeutic and natural products. 6 Among these, the oxazolecontaining amino acids are quite ubiquitous in various naturally occurring peptides, [7][8][9][10][11][12] which possess potential antibiotic and antitumor activity. 13,14 Such compounds have also been used to modify the bioactivity of other macromolecules.…”

Section: Introductionmentioning

confidence: 99%

Unraveling the protonation site of oxazole and solvation with hydrophobic ligands by infrared photodissociation spectroscopy

Chatterjee

Dopfer

2019

Phys. Chem. Chem. Phys.

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Section: Introductionmentioning

confidence: 99%

Unraveling the protonation site of oxazole and solvation with hydrophobic ligands by infrared photodissociation spectroscopy

Chatterjee

Dopfer

2019

Phys. Chem. Chem. Phys.

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“…Additionally, the three ring systems of furan or thiophene 87 which had the oxazole rings substituted 87 at their 2-and 5-positions, were also successfully obtained from the di-formyl substrates 86 (Scheme 21, bottom). This reaction was suitable for different aldehydes with furan or thiophene since both these oxazole synthetic methods occurred with good to excellent yield [61]. At the same year, the Georgiades group found that oligomeric chemical compounds composed by successive N,O-heteroaromatic rings, could be introduced for products with useful and mild properties as alternative substances for biomolecular recognition.…”

Section: Developments Of the Van Leusen Oxazole Synthesismentioning

confidence: 99%

“…Additionally, the three ring systems of furan or thiophene 87 which had the oxazole rings substituted 87 at their 2and 5-positions, were also successfully obtained from the di-formyl substrates 86 (Scheme 21, bottom). This reaction was suitable for different aldehydes with furan or thiophene since both these oxazole synthetic methods occurred with good to excellent yield[61].Molecules 2020, 25, x FOR PEER REVIEW 12 of Synthesis of C3-symmetric star-shaped molecules 83. In 2017, Civcir et al found a new application of the van Leusen reaction.…”

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confidence: 99%

“…By following this reaction, oxazole derivatives 85 with corresponding heterocyclic cores, were provided through the reaction of suitable 2-formyl substituted furan or thiophene derivatives 84 with TosMIC 25 (Scheme 21, top).Additionally, the three ring systems of furan or thiophene 87 which had the oxazole rings substituted 87 at their 2-and 5-positions, were also successfully obtained from the di-formyl substrates 86 (Scheme 21, bottom). This reaction was suitable for different aldehydes with furan or thiophene since both these oxazole synthetic methods occurred with good to excellent yield[61]. Synthesis of heterocyclic systems derivatives 85 and 87 based on TosMIC.…”

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confidence: 99%

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Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

2020

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Oxazole compounds, including one nitrogen atom and one oxygen atom in a five-membered heterocyclic ring, are present in various biological activities. Due to binding with a widespread spectrum of receptors and enzymes easily in biological systems through various non-covalent interactions, oxazole-based molecules are becoming a kind of significant heterocyclic nucleus, which have received attention from researchers globally, leading them to synthesize diverse oxazole derivatives. The van Leusen reaction, based on tosylmethylisocyanides (TosMICs), is one of the most appropriate strategies to prepare oxazole-based medicinal compounds. In this review, we summarize the recent advances of the synthesis of oxazole-containing molecules utilizing the van Leusen oxazole synthesis from 1972, aiming to look for potential oxazole-based medicinal compounds, which are valuable information for drug discovery and synthesis.

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“…As can be seen, isoxazole compounds ( 296 , 299 , 301 , 305 , 307 , 310 , 313 , 316 ) are obtained from the reactions of the intermediate formed with DMF‐DMA with hydroxylamine. Some examples of synthesis of hybrid molecules based on isoxazole based via similar mechanism are listed below [7,10,51,53,55,71–73] . (Scheme 40, 41).…”

Section: Formation Of Heterocycle Structures By Dmf‐dma Reactionsmentioning

confidence: 99%

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Gümüş

Koca

2020

ChemistrySelect

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N,N‐Dimethylformamide dimethyl acetal (DMF‐DMA) reagent can react with different functional groups of organic compounds. Enamines and dimethylamino imines are obtained, when the DMF‐DMA reagent is reacted with methylene, methyl and amino groups. These products are formed in the intermediate step in the synthesis of many hetero rings. These compounds are especially used as a starting material in the synthesis of heterostructures such as pyrimidine, pyridine, pyrazole, etc. Therefore, DMF‐DMA has been particularly prominent as a reagent in targeted synthesis and designs of many heterocyclic compounds. Herein, the reactions of DMF‐DMA reagent with different functional groups are categorized in four classes (methylene, methyl, amino, other groups) and the reactions of obtained enamine and dimethylamino imine compounds are investigated in detail such as nucleophilic addition, intramolecular cyclization or condensation reactions. The synthesis and continuation reactions of the enamine and dimethylamino imine compounds are also examined in terms of experimental conditions and reagents used.

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Experimental and theoretical investigation of new furan and thiophene derivatives containing oxazole, isoxazole, or isothiazole subunits

Cited by 17 publications

References 75 publications

Unraveling the protonation site of oxazole and solvation with hydrophobic ligands by infrared photodissociation spectroscopy

Unraveling the protonation site of oxazole and solvation with hydrophobic ligands by infrared photodissociation spectroscopy

Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

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