Tag: M.W=200-250

Jiang, Ruihang published the artcileSynthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid, Application In Synthesis of 2251-79-8, the publication is Synthetic Communications (2018), 48(20), 2652-2662, database is CAplus.

The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles I (R = Ph, 2-chlorophenyl, oxanthren-2-yl, etc.), triazoles II [R¹ = 2,4-Cl₂, 3-OH, 4-(CH₃)₂CH, etc.], and imidazolines III (R² = 3-methoxyphenyl, benzyl, 4-trifluoromethylphenyl, etc.). The magnetic silica sphere grafted sulfonic acid (MSS-SO₃H) is suitable for the synthesis of 1,2,3-triazoles I via the cycloaddition of nitroalkenes R¹C₆H₄CH=CHNO₂ with NaN₃, whereas the zinc-modified silica sphere catalyst (MSS-SO₃Zn) is more suitable for the synthesis of tetrazoles I. The MSS-SO₃Zn catalyst also works well for the synthesis of 2-substituted imidazolines III via the condensation of nitriles R²CN with ethylenediamine. Both MSS-SO₃H and MSS-SO₃Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.

Synthetic Communications 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, Application In Synthesis of 2251-79-8.

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

Tuellmann, Carl Phillip published the artcilePreparation and Reactions of (1H-Tetrazol-5-yl)zinc Pivalates, Product Details of C8H5F3N4, the publication is Synthesis (2020), 52(16), 2357-2363, database is CAplus.

The preparation and reactivity of new solid heterocyclic organozinc reagents, namely N-protected (1H-tetrazol-5-yl)zinc pivalates I (R = benzyl, (4-methoxyphenyl)methyl; R¹ = [(2,2-dimethylpropanoyl)oxy]zincio), as storable solids with appreciably air and moisture stability are reported. They are obtained in high yields from protected 1H-tetrazoles I (R¹ = H) by deprotonation using the mixed zinc-magnesium base TMPZnCl.Mg(OPiv)₂ (abbreviated as TMPZnOPiv; TMP = 2,2,6,6-tetramethylpiperidyl). Subsequent cross-couplings and copper-catalyzed electrophilic aminations using hydroxylamine benzoates BzOR¹ (R¹ = 3-[ethoxy(oxo)methane]piperidin-1-yl, 4-(pyrimidin-2-yl)piperazin-1-yl, [(1R,4R)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl](methyl)aminyl, (3-[4-[(2,6-difluorophenyl)carbonyl]phenyl]propyl)(2-phenylethyl)aminyl) give access to functionalized 1H-tetrazoles while tolerating many functional groups.

Synthesis 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 C21H33N5O7, Product Details of C8H5F3N4.

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

Rajamanickam, Suresh published the artcileIntermolecular CDC amination of remote and proximal unactivated C_sp³-H bonds through intrinsic substrate reactivity – expanding towards a traceless directing group, Application In Synthesis of 2251-79-8, the publication is Chemical Science (2021), 12(46), 15318-15328, database is CAplus and MEDLINE.

An intermol. radical based distal selectivity in appended alkyl chains, e.g., I has been developed. The selectivity is maximum when the distal carbon is γ to the appended group and decreases by moving from γ → δ → ε positions. In -COO- linked alkyl chains, the same distal γ-selectivity is observed irresp. of its origin, either from the alkyl carboxy acid or alkyl alc. The appended groups include esters, N-H protected amines, phthaloyl, sulfone, sulfinimide, nitrile, phosphite, phosphate and borate esters. In borate esters, boron serves as a traceless directing group, which is hitherto unprecedented for any remote C_sp³-H functionalization. The selectivity order follows the trend: 3° benzylic > 2° benzylic > 3° tertiary > α to keto > distal methylene (γ > δ > ε). Computations predicted the radical stability (thermodn. factors) and the kinetic barriers as the factors responsible for such trends. Remarkably, this strategy eludes any designer catalysts, and the selectivity is due to the intrinsic substrate reactivity.

Chemical Science 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, Application In Synthesis of 2251-79-8.

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

Vergani, Barbara published the artcileNovel Benzohydroxamate-Based Potent and Selective Histone Deacetylase 6 (HDAC6) Inhibitors Bearing a Pentaheterocyclic Scaffold: Design, Synthesis, and Biological Evaluation, Synthetic Route of 2251-79-8, the publication is Journal of Medicinal Chemistry (2019), 62(23), 10711-10739, database is CAplus and MEDLINE.

Histone deacetylase 6 (HDAC6) is a peculiar HDAC isoform whose expression and functional alterations were correlated with a variety of pathologies such as autoimmune disorders, neurodegenerative diseases, and cancer. It is primarily a cytoplasmic protein, and its deacetylase activity is focused mainly on non-histone substrates such as tubulin, heat shock protein (HSP)90, Foxp3 and cortactin, to name a few. Selective inhibition of HDAC6 does not show cytotoxic effects in healthy cells, normally associated with the inhibition of Class I HDAC isoforms. Here the authors describe the design and synthesis of a new class of potent and selective HDAC6 inhibitors that bear a pentaheterocyclic central core. These compounds show a remarkably low toxicity both in vitro and in vivo and are able to increase the function of regulatory T cells (Tregs) at well tolerated concentrations, suggesting a potential clin. use for the treatment of degenerative, auto-immune diseases and organ transplantation.

Journal of Medicinal 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 C8H5F3O2S, Synthetic Route of 2251-79-8.

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

Rajamanickam, Suresh published the artcileBu₄NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters, Formula: C8H5F3N4, the publication is Journal of Organic Chemistry (2020), 85(4), 2118-2141, database is CAplus and MEDLINE.

Bu₄NI-catalyzed regioselective N²-methylation, N²-alkylation, and N²-arylation of tetrazoles have been achieved using tert-Bu hydroperoxide (TBHP) as the Me source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin d., transition-state barriers (kinetic control), and thermodn. stability of the products (thermodn. control) play essential roles in the observed regioselectivity during N-alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

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, Formula: C8H5F3N4.

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

Gutmann, Bernhard published the artcileSynthesis of 5-Substituted 1H-Tetrazoles from Nitriles and Hydrazoic Acid by Using a Safe and Scalable High-Temperature Microreactor Approach, Name: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, the publication is Angewandte Chemie, International Edition (2010), 49(39), 7101-7105, S7101/1-S7101/12, database is CAplus and MEDLINE.

A general and scalable method for the continuous flow synthesis of 5-substituted 1H-tetrazole derivatives via addition of HN₃ to organic nitriles is described. Key to this process is the in situ generation of HN₃ from NaN₃ and acetic acid in a microreactor coupled to an intensified high-temperature/high-pressure flow addition step to the nitrile. Under optimized conditions, tetrazole compounds are formed with quant. conversion in residence times of a few minutes, providing excellent purities and yields of isolated product.

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, Name: 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole.

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

Sridhar, Madabhushi published the artcileOne-step synthesis of 5-substituted 1H-tetrazoles from an aldehyde by reaction with acetohydroxamic acid and sodium azide under Bi(OTf)₃ catalysis, COA of Formula: C8H5F3N4, the publication is Synthesis (2013), 45(4), 507-510, database is CAplus.

An efficient one-step method for the synthesis of 5-substituted 1H-tetrazoles from aldehydes by reaction with acetohydroxamic acid and sodium azide using bismuth(III) triflate as the catalyst is described.

Synthesis 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 C10H7NO3, COA of Formula: C8H5F3N4.

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

Joshi, Sameer M. published the artcileThe microwave-assisted synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition over a heterogeneous Cu-based catalyst: application to the preparation of ¹³N-labelled tetrazoles, Safety of 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole, the publication is New Journal of Chemistry (2017), 41(16), 8084-8091, database is CAplus.

The [3+2] cycloaddition between various nitriles and sodium azide proceeded smoothly in the presence of a new Cu^II catalyst in N-methyl-2-pyrrolidone (NMP) to give the corresponding 5-substituted 1H-tetrazoles. The desired tetrazoles were obtained in high yields within 3-30 min by employing controlled microwave heating. The reaction most probably proceeded through the activation of the nitrile groups by the Cu^II species, followed by a successive [3+2] cycloaddition with the sodium azide. The good performance of the catalyst enabled the preparation of selected tetrazoles labeled with the positron emitter nitrogen-13 even under conventional heating. The short reaction time, simple work-up procedure, and recyclability of the catalyst were advantages of the method reported here.

New Journal of 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, Safety of 5-(4-(Trifluoromethyl)phenyl)-1H-tetrazole.

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

Green, Luke published the artcileUV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow, Formula: C8H5F3N4, the publication is Chemistry – A European Journal (2020), 26(65), 14866-14870, database is CAplus and MEDLINE.

A range of 1,3,4-oxadiazoles I (R¹ = cylopropanyl, C₆H₅, 2-MeOC₆H₄, 4-FC₆H₄, etc.; R² = Me, C₆H₅, 4-MeC₆H₄, 2-furanyl, etc.) have been synthesized using a UV-B light activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.

Chemistry – A European Journal 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, Formula: C8H5F3N4.

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