Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides

Zhang, Xiaoxiang; Teo, Wan Teng; Chan, Philip Wai Hong

doi:10.1016/j.jorganchem.2010.09.059

Cited by 52 publications

(6 citation statements)

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“…Uemura and co-workers rst reported the synthesis of oxazole by employing a dual diruthenium (II,III) and gold(III) catalytic system. 140,203 Following this work, Liu and Kumar demonstrated a dual ruthenium(III) and zinc(II) catalyst combination could also mediate the cyclization of propargylic alcohols with amides that afforded the oxazole product in excellent yields. 204 More recently, Zhan and co-workers described a Brønsted acidmediated synthesis of oxazole that could be achieved in the presence of a stoichiometric amount of p-TsOH$H 2 O.…”

Section: Ytterbium Derived Catalystsmentioning

confidence: 93%

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Scope and advances in the catalytic propargylic substitution reaction

2018

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Section: Ytterbium Derived Catalystsmentioning

confidence: 93%

“…Chan and co-workers in the year 2011 reported a Yb(OTf) 3 catalyzed cyclization of trisubstituted propargylic alcohols 39 with aryl amides 77 towards the synthesis of di- and trisubstituted 2-aryloxazoles 336, Scheme 164 . 203 …”

Section: Different Catalysts Used In Propargylic Substitution Reactionsmentioning

confidence: 99%

Scope and advances in the catalytic propargylic substitution reaction

2018

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“…In 2011, the group of Davies reported a regioselective gold-catalyzed intermolecular [3 + 2] cycloaddition for the synthesis of 2,4,5-trisubstituted oxazoles 190 employing conjugated N -ylides 188 as N -nucleophilic N -acyl nitrene/1,3- N,O -dipole equivalents and ynamides 189 (Scheme ). The application of [3 + 2] cycloaddition across C–C π systems for the preparation of 1,3-oxazoles is extremely limited , whereas it has been widely employed for the preparation of other heterocycles. , …”

Section: Generation Of 15- 16- and 17-dipolesmentioning

confidence: 99%

Gold-Containing and Gold-Generated 1,n-Dipoles as Useful Platforms toward Cycloadditions and Cyclizations

2012

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Some of the most synthetically useful methods to construct molecular complexity include Diels−Alder, [1,3]-dipolar-and [m+n]-cycloadditions. In this context, the efficient generation of 1,n-dipoles plays a key role. Dipoles have been usually described as transient, difficult to harness species toward cycloaddition reactions. This review highlights the development of new methodologies for the efficient generation of these valuable intermediates by means of gold catalysis, and their application in the construction of small-medium size carbocycles. The mechanistic rationale underlying these transformations is also presented here.

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“…Amides production is one of the most essential processes of the pharmaceutical and chemical industries . These types of molecules are extensively utilized as building blocks in the preparation of pharmaceuticals, pigments, agrochemicals, photographic products, and polymers. − About 30% of drug molecules have at least one amide linked, demonstrating its relevance in drug design and the pharmaceutical industry …”

Section: Introductionmentioning

confidence: 99%

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Chaparro

Rojas

Castillo

et al. 2020

ACS Sustainable Chem. Eng.

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Biogenic carbonates were studied as catalysts in this work for the direct synthesis of amides under solvent-free conditions. Solids were synthesized by microbial coprecipitation of CaCl 2 and Ni salts and Cu and Fe salts. The catalysts were characterized by thermogravimetric analysis, nitrogen physisorption measurements, X-ray diffraction, and X-ray photoelectron spectroscopy. The polymorphism, hydrophilicity, and textural properties depended on the metal oxides type incorporated on CaCO 3 . N-Arylsuccinimides synthesis was employed as test reaction, obtaining remarkable selectivity and conversion in the reaction of succinic acid with p-toluidine and aniline, respectively. Optimized conditions were subsequently extended to the solvent-free synthesis of diverse amides in good yields using CuO−CaCO 3 as the catalyst in air. The direct amidation protocol was amenable to the use of different primary amines and nonactivated carboxylic acids.

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Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides

Cited by 52 publications

References 44 publications

Scope and advances in the catalytic propargylic substitution reaction

Scope and advances in the catalytic propargylic substitution reaction

Gold-Containing and Gold-Generated 1,n-Dipoles as Useful Platforms toward Cycloadditions and Cyclizations

Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

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Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides

Cited by 52 publications

References 44 publications

Scope and advances in the catalytic propargylic substitution reaction

Scope and advances in the catalytic propargylic substitution reaction

Gold-Containing and Gold-Generated 1,n-Dipoles as Useful Platforms toward Cycloadditions and Cyclizations

Solventless Amide Synthesis Catalyzed by Biogenic CaCO3 Materials

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Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials