Improvement of the Van Leusen reaction in the presence of β-cyclodextrin: a green and efficient synthesis of oxazoles in water

Rahimzadeh, Golnaz; Kianmehr, Ebrahim; Mahdavi, Mohammad

doi:10.1515/znb-2017-0005

Cited by 8 publications

(4 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction between TosMIC 63 and benzaldehyde 64 was carried out in the presence of various amounts of Et 3 N and β-CD (β-Cyclodextrin) at 50°C in water (Figure 17). The simple procedure, relatively short reaction times, easy workup and high yields are the reasons that promote the use of β-CD/water as an inexpensive and environmentally benign catalyst for the synthesis of differently substituted oxazoles [25,26].…”

Section: Miscellaneousmentioning

confidence: 99%

Synthesis of Five-Membered Heterocycles Using Water as a Solvent

Kathuria,

Jahan,

Dwivedi

2023

Strategies for the Synthesis of Heterocycles and Their Applications

View full text Add to dashboard Cite

Water owing to its modest cost, easy accessibility, and non-toxic and non-flammable attributes has been considered one of the most ideal and promising solvents in organic synthesis, especially from the green and sustainable point of view. Furthermore, considering the immense enzyme-mediated biosynthesis in nature, water serves as a favourable medium for the versatile synthesis of a wide variety of complicated molecules and compounds. Over the past decades, considerable efforts have been deployed in conducting organic reactions using water as a solvent. In recent years, more and more general organic reactions were successfully exploited to perform in water instead of organic solvents to achieve sustainable and environmental benefits.

show abstract

Section: Miscellaneousmentioning

confidence: 99%

Synthesis of Five-Membered Heterocycles Using Water as a Solvent

Kathuria,

Jahan,

Dwivedi

2023

Strategies for the Synthesis of Heterocycles and Their Applications

View full text Add to dashboard Cite

show abstract

“…It was clearly assured that the oxazole 81 was formed in an excellent yield through the analysis of the reaction mixtures. This novel approach improves the van Leusen reaction greatly since the catalytic amounts of base can be used to promote the reaction at low temperatures and water can be acted as a green media for this reaction (Scheme 19) [59]. In 2017, Mahdavi's group described an efficient protocol for the formation of oxazoles.…”

Section: Developments Of the Van Leusen Oxazole Synthesismentioning

confidence: 99%

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

2020

View full text Add to dashboard Cite

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.

show abstract

“…Due to their biological importance, 5-membered heterocyclic compounds with the 1,3-oxazole ring, have been obtained over time by a variety of chemical synthesis methods [37][38][39][40][41]. To date, the most widely used methodologies for preparation of these compounds include the condensation of cyanohydrins (formed from aromatic aldehydes) and aromatic aldehydes in the dry ether in the presence of anhydrous hydrogen chloride (Fischer synthesis) [42], Cornforth rearrangement [43], the reaction of aldehydes with p-toluene-sulfonylmethyl isocyanide (van Leusen synthesis) [37,44], Doyle reaction of nitriles with diazocarbonyl compounds [45], Robinson-Gabriel synthesis which involves cyclodehydration of N-acyl-α-amino ketones [46,47]. Other synthetic methods are the coupled Ugi and Robinson-Gabriel reaction between primary amines, carbonyl compounds, carboxylic acids, and isocyanides to afford the corresponding functionalized α-acylamino amides followed by their cyclodehydration [48], Friedel-Crafts/Robinson-Gabriel synthesis using 1,3-oxazol-5(4H)-one templates in presence of AlCl3 as the Friedel-Crafts catalyst and trifluoromethanesulfonic acid as the Robinson-Gabriel cyclodehydrating agent [49], Dakin-West reaction of N-acyl-α-amino acids with carboxylic anhydrides in the presence of a weak base, such as pyridine [50], reaction of Nacyl-α-amino acids with di-tert-butyl dicarbonate [51], Blümlein-Lewy method which consists in the condensation of amides with α-halo or α-hydroxy ketones [52], etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Cytotoxicity Evaluation of New Diphenyl Sulfone Derivatives

Apostol¹

2021

FARMACIA

View full text Add to dashboard Cite

Taking into account that the substituted diphenyl sulfone is an important pharmacophore in medicinal chemistry, in this paper, we report the synthesis, characterization, and cytotoxicity evaluation of seven new compounds: six ethyl 1,3-oxazol-5yl carbonates and an acyclic product (ethyl ester of an N-acyl-α-amino acid), containing the arylsulfonylphenyl moiety. The synthesized compounds were characterized by elemental analysis and spectral techniques (UV-Vis, FT-IR, MS, 1 H-NMR, 13 C-NMR). Their purity was checked by reversed phase HPLC. The cytotoxic effect of new compounds was assessed using Daphnia magna bioassay. RezumatLuând în considerare faptul că difenilsulfona substituită este un farmacofor important în chimia medicală, în această lucrare este descrisă sinteza, caracterizarea și evaluarea citotoxicității a șapte compuși noi: șase carbonați de etil 1,3-oxazol-5-il și un produs aciclic (esterul etilic al unui N-acil-α-aminoacid), care conțin fragmentul arilsulfonilfenil. Compușii sintetizați au fost caracterizați prin analiză elementală și tehnici spectrale (UV-Viz, FT-IR, SM, 1 H-RMN, 13 C-RMN). Puritatea lor a fost verificată prin HPLC cu fază inversă. Efectul citotoxic al noilor compuși a fost evaluat utilizând testul biologic Daphnia magna.

show abstract

Improvement of the Van Leusen reaction in the presence of β-cyclodextrin: a green and efficient synthesis of oxazoles in water

Cited by 8 publications

References 30 publications

Synthesis of Five-Membered Heterocycles Using Water as a Solvent

Synthesis of Five-Membered Heterocycles Using Water as a Solvent

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

Synthesis, Characterization and Cytotoxicity Evaluation of New Diphenyl Sulfone Derivatives

Contact Info

Product

Resources

About