Tag: M.W=200-250

Treitler, Daniel S. published the artcileDevelopment and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles, Related Products of isoxazole, the publication is Organic Process Research & Development (2017), 21(3), 460-467, database is CAplus.

The search for a faster, safer protocol for the direct synthesis of 5-aryltetrazoles from aryl nitriles in the presence of sodium azide and an amine hydrochloride salt led to the discovery of a buffered system comprised of BnNH₂, BnNH₂·HCl, and NaN₃. After optimization of reaction conditions and a thorough study of reaction safety, the procedure was demonstrated for the synthesis of several hundred grams of 4-chloro-2-(2H-tetrazol-5-yl)phenol. The generality of the developed reaction conditions was established by a small-scale reactivity screen using 16 addnl. aryl and heteroaryl nitrile substrates.

Organic Process Research & Development published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H16O2, Related Products of isoxazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Aridoss, Gopalakrishnan published the artcileHighly Efficient Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Cu-Zn Alloy Nanopowder, Conversion into 1,5- and 2,5-Disubstituted Tetrazoles, and Synthesis and NMR Studies of New Tetrazolium Ionic Liquids, SDS of cas: 2251-79-8, the publication is European Journal of Organic Chemistry (2011), 2011(31), 6343-6355, S6343/1-S6343/57, database is CAplus.

A series of 5-substituted 1H-tetrazoles were synthesized through [3+2] cycloaddition reactions between nitriles RCN and NaN₃ in the presence of Cu-Zn alloy nanopowder as catalyst. The 1,5-di-Bu, 1-butyl-5-hexyl, 2,5-di-Bu, and 2-butyl-5-hexyl derivatives were then used as building blocks to synthesize several novel tetrazolium ionic liquids (ILs) with EtSO₄^–, OTf^–, and NTf₂^– counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approx. 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and Et sulfate salts are room-temperature ILs that are hydrophilic, whereas the NTf₂ salts are low-melting ILs and are hydrophobic. The resulting tetrazolium-based ionic liquids were studied by various multinuclear and 2D NMR techniques including natural abundance ¹⁵N and ¹H/¹⁵N correlations.

European Journal of Organic Chemistry published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, SDS of cas: 2251-79-8.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Sreedhar, B. published the artcileCuFe₂O₄ nanoparticles: a magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1H-tetrazoles, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, the publication is Tetrahedron Letters (2011), 52(28), 3565-3569, database is CAplus.

An efficient and economical protocol for the synthesis of 5-substituted 1H-tetrazoles from various nitriles and sodium azide is described using magnetically recoverable and reusable CuFe₂O₄ nanoparticles. A wide variety of aryl nitriles underwent [2+3] cycloaddition under mild reaction conditions to afford tetrazoles in good to excellent yields. The catalyst was magnetically separated and reused five times without significant loss of catalytic activity.

Tetrahedron Letters published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C12H9N3O4, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Sharma, Swagat published the artcileDiscovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators, SDS of cas: 2251-79-8, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(6), 791-796, database is CAplus and MEDLINE.

The study described the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-yl acetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, a tetrazole scaffold was identified that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, the compounds were evaluated in Tier 1 DMPK assays and identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.

Bioorganic & Medicinal Chemistry Letters published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C13H10O3, SDS of cas: 2251-79-8.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Reichart, Benedikt published the artcileHigh-temperature continuous flow synthesis of 1,3,4-oxadiazoles via N-acylation of 5-substituted tetrazoles, Category: isoxazole, the publication is Tetrahedron Letters (2012), 53(8), 952-955, database is CAplus.

Applying continuous flow processing in a high-temperature/high-pressure regime (200-220°, 11-14 bar) 2,5-disubstituted-1,3,4-oxadiazoles are prepared in high yields within 5-10 min residence time by treatment of 5-substituted-1H-tetrazoles with anhydrides or acid chlorides as electrophiles (Huisgen reaction).

Tetrahedron Letters published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Category: isoxazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Esmaeilpour, Mohsen published the artcileFacile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe₃O₄@SiO₂ nanoparticles, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, the publication is Journal of Molecular Catalysis A: Chemical (2014), 18-29, database is CAplus.

A new method for preparing functionalized superparamagnetic Fe₃O₄@SiO₂ possessing high saturation magnetization was reported. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe₃O₄@SiO₂ nanosphere was synthesized by using nano Fe₃O₄ as the core, TEOS as the silica source and polyethylene glycol (PEG 1000) as the surfactant. Then, the silica-coated Fe₃O₄ nanoparticles were covered with ligand complex of Cu(II). The functionalized magnetic core-shell nanoparticles (MNPs) were investigated by Fourier transform IR spectroscopy, transmission electron microscopy, SEM, X-ray diffraction, thermogravimetric anal., dynamic light scattering and N₂ adsorption/desorption. Also, its Cu content was determined by inductively coupled plasma (ICP) analyzer. Then, the immobilized copper complex was used as an efficient catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines in good to excellent yields. The results show that the supported catalyst could be conveniently recovered through the use of an external magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.

Journal of Molecular Catalysis A: Chemical published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Recommanded Product: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Nakamuro, Takayuki published the artcileEnantioselective Denitrogenative Annulation of 1H-Tetrazoles with Styrenes Catalyzed by Rhodium, HPLC of Formula: 2251-79-8, the publication is Angewandte Chemie, International Edition (2018), 57(19), 5497-5500, database is CAplus and MEDLINE.

Sulfonylation of 1H-tetrazoles with triflic anhydride in the presence of chiral rhodium(II) carboxylate dimers causes denitrogenation to generate α-azo rhodium(II) carbenoid species as new types of donor/acceptor carbenoids, which then readily react with styrenes to afford 3,5-diaryl-2-pyrazolines with a high degree of enantioselectivity. Thus, e.g., reaction of 5-phenyl-1H-tetrazole with styrene and Tf₂O in presence of 2,4,6-tri-tert-butylpyridine and a chiral Rh₂L₄ complex in ethylcyclohexane afforded I (84%, 96% ee).

Angewandte Chemie, International Edition published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, HPLC of Formula: 2251-79-8.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Miura, Tomoya published the artcileRegioselective 1,3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles, Quality Control of 2251-79-8, the publication is Chemistry Letters (2021), 50(1), 131-135, database is CAplus.

A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles was reported. When 5-aryltetrazoles were triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generated N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately underwent 1,3-dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.

Chemistry Letters published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Quality Control of 2251-79-8.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Cantillo, David published the artcileAn Experimental and Computational Assessment of Acid-Catalyzed Azide-Nitrile Cycloadditions, Product Details of C8H5F3N4, the publication is Journal of Organic Chemistry (2012), 77(23), 10882-10890, database is CAplus and MEDLINE.

The mechanism of the azide-nitrile cycloaddition mediated by different Bronsted and Lewis acids has been addressed through DFT calculations In all cases activation of the nitrile substrate by the Bronsted or Lewis acid catalyst was found to be responsible for the rate enhancement. According to DFT calculations the cycloaddition proceeds in a stepwise fashion involving the initial formation of an open-chain imidoyl azide intermediate. Kinetic experiments performed using N-methyl-2-pyrrolidone as solvent and sodium azide as azide source demonstrate that all evaluated Bronsted acids have the same efficiency toward cycloaddition with benzonitrile, suggesting that hydrazoic acid is the actual dominant catalytic species in these tetrazole syntheses. Lewis acids such as Zn or Al salts perform in a similar manner, activating the nitrile moiety and leading to an open-chain intermediate that subsequently cyclizes to produce the tetrazole nucleus. The most efficient catalyst evaluated was 5-azido-1-methyl-3,4-dihydro-2H-pyrrolium azide, which can readily be generated in situ from aluminum chloride, sodium azide in N-methyl-2-pyrrolidone. The efficiency of this catalyst has been examined by preparation of a series of 5-substituted-1H-tetrazoles. The desired tetrazole structures were obtained in high yields within 3-10 min employing controlled microwave heating.

Journal of Organic Chemistry published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Product Details of C8H5F3N4.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem

Cantillo, David published the artcileMechanistic Insights on Azide-Nitrile Cycloadditions: On the Dialkyltin Oxide-Trimethylsilyl Azide Route and a New Vilsmeier-Haack-Type Organocatalyst, Computed Properties of 2251-79-8, the publication is Journal of the American Chemical Society (2011), 133(12), 4465-4475, database is CAplus and MEDLINE.

The mechanism of the azide-nitrile cycloaddition mediated by the known dialkylltin oxide-trimethylsilyl azide catalyst system was addressed through DFT calculations The catalytic cycle for this tin/silicon complex-based mechanism was thoroughly examined, disclosing the most plausible intermediates and the energetics involved in the rate enhancement. A new catalyst, 5-azido-1-methyl-3,4-dihydro-2H-pyrrolium azide, is presented for the formation of tetrazoles by cycloaddition of sodium azide with organic nitriles under neutral conditions. The efficiency of this organocatalyst, generated in situ from N-methyl-2-pyrrolidone (NMP), sodium azide, and trimethylsilyl chloride under reaction conditions, was examined by preparation of 5-substituted-1H-tetrazoles. The desired target structures were obtained in high yields within 15-25 min employing controlled microwave heating. An in depth computational anal. of the proposed catalytic cycle also was addressed to understand the nature of the rate acceleration. The computed energy barriers were compared to the dialkylltin oxide-trimethylsilyl azide metal-based catalyst system. Both the tin/silicon species and the new organocatalyst accelerate the azide-nitrile coupling by activating the nitrile substrate. As compared to the dialkylltin oxide-trimethylsilyl azide method, the organocatalytic system presented herein has the advantage of higher reactivity, in situ generation from inexpensive materials, and low toxicity.

Journal of the American Chemical Society published new progress about 2251-79-8. 2251-79-8 belongs to isoxazole, auxiliary class Trifluoromethyl,Fluoride,Benzene, name is 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, and the molecular formula is C8H5F3N4, Computed Properties of 2251-79-8.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
Isoxazole | C3H3NO – PubChem