TiO<sub>2</sub>‐Nanoparticles Catalyzed Synthesis of New Trifluoromethyl‐4,5‐dihydro‐1,2,4‐oxadiazoles and Trifluoromethyl‐1,2,4‐oxadiazoles

Darehkordi, Ali; Ramezani, Mohammad; Rahmani, Fariba

doi:10.1002/jhet.3207

Cited by 11 publications

(2 citation statements)

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“…Darehkordi and co-workers disclosed a TiO 2 -nanoparticlecatalyzed synthesis of trifluoromethyl-4,5-dihydro-1,2,4-oxadiazoles and trifluoromethyl-1,2,4-oxadiazoles from the reaction of trifluoroacetimidoyl chlorides and amidoximes (Scheme 52). 69 Changing the reaction condition regarding solvent and base, different trifluoromethyl-substituted N-heterocycle products were obtained. The reaction was considered to be initiated by the activation of imidoyl chlorides by TiO 2 -NPs to result in a TiO 2 -imidoyl complex, which was attacked by the nucleophilic oxygen atom of amidoxime.…”

Section: Synthesis Of Fluoroalkyl 5-membered N-heterocyclesmentioning

confidence: 99%

Trifluoroacetimidoyl halides: a potent synthetic origin

Chen

2020

Org. Chem. Front.

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Section: Synthesis Of Fluoroalkyl 5-membered N-heterocyclesmentioning

confidence: 99%

Trifluoroacetimidoyl halides: a potent synthetic origin

Chen

2020

Org. Chem. Front.

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“…Darehkordi and colleagues reported the synthesis of a new series of trifluoromethyl-1,2,4-oxadiazoles ( Scheme 43 ) [ 147 ]. 3-Aryl-5-(trifluoromethyl)-1,2,4-oxadiazoles were synthesized by reaction of aryl amidoximes and trifluoroacetimidoyl chlorides in a one-pot manner in the presence of NaH and titanium dioxide nanoparticle as the catalyst.…”

Section: Miscellaneousmentioning

confidence: 99%

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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1,2,4-Oxadiazole is an essential motif in drug discovery represented in many experimental, investigational, and marketed drugs. This review covers synthetic methods that allow the conversion of different types of organic compounds into 1,2,4-oxadiazole at ambient temperature and the practical application of the latter approaches for the preparation of pharmaceutically important molecules. The discussed methods are divided into three groups. The first combines two-stage protocols requiring the preliminary preparation of O-acylamidoximes followed by cyclization under the action of organic bases. The advantages of this route are its swiftness, high efficiency of the cyclization process, and uncomplicated work--up. However, it requires the preparation and isolation of O-acylamidoximes as a separate preliminary step. The second route is a one-pot synthesis of 1,2,4-oxadiazoles directly from amidoximes and various carboxyl derivatives or aldehydes in aprotic bipolar solvents (primarily DMSO) in the presence of inorganic bases. This recently proposed pathway proved to be highly efficient in the field of medicinal chemistry. The third group of methods consists of diverse oxidative cyclizations, and these reactions have found modest application in drug design thus far. It is noteworthy that the reviewed methods allow for obtaining 1,2,4-oxadiazoles with thermosensitive functions and expand the prospects of using the oxadiazole core as an amide- or ester-like linker in the design of bioactive compounds.

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An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

Shenbagapushpam¹,

Muthukumar²,

Yuvaraj

et al. 2021

ChemistrySelect

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A heterogeneous and hard bound TiIV anchored MCM‐41 material has been successfully evaluated for catalytic applications in the one pot synthesis of highly functionalized β‐amino ketones and quinoline appended π‐conjugated imines via Mannich reaction and condensation reaction, respectively. The synthetic transformation was successfully catalyzed via the dual Bronsted and Lewis acetic nature of the Ti‐MCM‐41 material that provided excellent yields of the desired products. The heterogeneous catalyst shows good catalytic performance, facile separation from the reaction mixture and can be reused in more than five catalytic cycles without any significant loss in the yield.

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TiO₂‐Nanoparticles Catalyzed Synthesis of New Trifluoromethyl‐4,5‐dihydro‐1,2,4‐oxadiazoles and Trifluoromethyl‐1,2,4‐oxadiazoles

Cited by 11 publications

References 34 publications

Trifluoroacetimidoyl halides: a potent synthetic origin

Trifluoroacetimidoyl halides: a potent synthetic origin

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

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TiO2‐Nanoparticles Catalyzed Synthesis of New Trifluoromethyl‐4,5‐dihydro‐1,2,4‐oxadiazoles and Trifluoromethyl‐1,2,4‐oxadiazoles

Cited by 11 publications

References 34 publications

Trifluoroacetimidoyl halides: a potent synthetic origin

Trifluoroacetimidoyl halides: a potent synthetic origin

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

An Efficient Synthesis of Heterogeneous and Hard Bound TiIV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

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Product

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About

TiO₂‐Nanoparticles Catalyzed Synthesis of New Trifluoromethyl‐4,5‐dihydro‐1,2,4‐oxadiazoles and Trifluoromethyl‐1,2,4‐oxadiazoles

An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines