Month: November 2022

Cabiddu, Salvatore et al. published their research in Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti in 1966 | CAS: 80348-66-9

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.HPLC of Formula: 80348-66-9

4-Isoxazolones was written by Cabiddu, Salvatore;Ricca, Aldo. And the article was included in Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti in 1966.HPLC of Formula: 80348-66-9 The following contents are mentioned in the article:

An attempt to extend the reaction used by Blatt and Hawkins (CA 29, 1591) for the synthesis of 4-isoxazoles is described. The compounds were synthesized by the following route: RCOCH2COR SO2Cl2→ RCOCHClCOR1 AcON2→ RCOCH(OAc)COR1 (I) NH2OH→ RC(:NOH)C(OAc):C(OH)R1 (II) → III. By this method the following III were obtained (R, R1, and m.p. and b.p./mm. of the Me ether given): Ph, Ph, 105 and 125°, -; Me, Me, 92-4 and 83°, 95-100°/12; Et, Et, b0.2 87-90°, 60-4°/30; Ph, Me, 11819°, 120°/0.5. The di-Ph and di-Me derivatives were obtained in 2 polymorphic forms. The treatment of II with NH2OH in a neutral medium permitted isolation of PhC(:NOH)CH(Oll)COMe and PhC(:NOH)CH(OH)COPh, m. 156-8°, in 84% yield, which upon acidification were immediately cyclized to the corresponding III. By the action of NH2OH on acetylacetonate in the presence of pyridine, the dioxime MeC(:NOH)CH(OAc)C(:NOH)Me, m. 157°, was obtained, which upon acid treatment underwent cyclization to give 3,5-dimethyl-4-isoxazole. All synthesized isoxazoles were sensitive to light and tended to be unstable on storage. All except the 3,5-di-Ph compound gave enolic reactions with FeCl3. This study involved multiple reactions and reactants, such as Isoxazol-4-ol (cas: 80348-66-9HPLC of Formula: 80348-66-9).

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.HPLC of Formula: 80348-66-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Umani-Ronchi, A. et al. published their research in Tetrahedron Letters in 1966 | CAS: 80348-66-9

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. The electrophilic cyclization of various 2-alkynone O-methyl oximes with a wide range of substrates such as ICl, I2, Br2, PhSeBr, etc. provides a variety of 3,4,5-trisubstituted isoxazoles in good to excellent yields.SDS of cas: 80348-66-9

Reaction between dimethyloxosulfonium methylide and benzonitrile oxide was written by Umani-Ronchi, A.;Bravo, P.;Gaudiano, G.. And the article was included in Tetrahedron Letters in 1966.SDS of cas: 80348-66-9 The following contents are mentioned in the article:

The reactivity of H2C–S+(O)Me2 (I) towards 1,3-dipoles was investigated to test the possibility of obtaining 4-membered heterocyclic rings. (I prepared in situ from Me3S(O)I or Me3S(O)Cl and NaH) treated with PhCNO in cold Me2SO gave a complex mixture from which 3-phenyl-2-isoxazoline (II), Ph vinyl ketone oxime (III), 3-phenyl-5-benzoyl-2-isoxazoline oxime (IV) and the Ph vinyl ketone oxime hydroxamie ester (V) were isolated. None of the unstable 3-phenyloxazetidine (VI) was isolated. The ylide brought about 2 consecutive transfers of CH2 to the substrate, probably through the zwitterion intermediate (VII) from which the compounds II-V may be readily derived. II was identified by anal., N.M.R. spectrum, and physicochem. characteristics. Addition of 2 molar equivalents I per molar equivalent PhNCO yielded up to 30% III, m. 85°, evidently the syn-Ph isomer. IV, m. 136°, was prepared by reaction of III with PhCNO. V, m. 126°, was also obtained in very small amount in the reaction of PhCNO with III. Beside the compounds II-V, many byproducts were obtained in small amounts PhCN, BzNH2 and BzOH originated from PhCNO by reductive and hydrolytic processes. The diphenylfuroxan (VIII) is a normal product of dimerization; BzNHOBz is a decomposition product of PhC(:NOH)Cl as well as of PhCNO itself under acid conditions: and the diphenyl-1,2,4-oxadiazole (IX) represents the product of the reaction between PhCNO and PhCN (CA 51, 15502e) according to Leandri and Pellotti. This study involved multiple reactions and reactants, such as Isoxazol-4-ol (cas: 80348-66-9SDS of cas: 80348-66-9).

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. The electrophilic cyclization of various 2-alkynone O-methyl oximes with a wide range of substrates such as ICl, I2, Br2, PhSeBr, etc. provides a variety of 3,4,5-trisubstituted isoxazoles in good to excellent yields.SDS of cas: 80348-66-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Nagy, Peter I. et al. published their research in International Journal of Molecular Sciences in 2016 | CAS: 80348-66-9

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Isoxazole can be synthesised via a variety of methods. Examples include via the reaction of hydroxylamine with 1,3-diketones or derivatives of propiolic acid.SDS of cas: 80348-66-9

Replacement of oxygen by sulfur in small organic molecules. 3. Theoretical studies on the tautomeric equilibria of the 2OH and 4OH-substituted oxazole and thiazole and the 3OH and 4OH-substituted isoxazole and isothiazole in the isolated state and in solution was written by Nagy, Peter I.. And the article was included in International Journal of Molecular Sciences in 2016.SDS of cas: 80348-66-9 The following contents are mentioned in the article:

This follow-up paper completes the author’s investigations to explore the in-solution structural preferences and relative free energies of all OH-substituted oxazole, thiazole, isoxazole, and isothiazole systems. The polarizable continuum dielec. solvent method calculations in the integral-equation formalism (IEF-PCM) were performed at the DFT/B97D/aug-cc-pv(q+(d))z level for the stable neutral tautomers with geometries optimized in dichloromethane and aqueous solution With the exception of the predictions for the predominant tautomers of the 3OH isoxazole and isothiazole, the results of the IEF-PCM calculations for identifying the most stable tautomer of the given species in the two selected solvents agreed with those from exptl. investigations. The calculations predict that the hydroxy proton, with the exception for the 4OH isoxazole and 4OH isothiazole, moves preferentially to the ring nitrogen or to a ring carbon atom in parallel with the development of a C=O group. The remaining, low-fraction OH tautomers will not be observable in the equilibrium compositions Relative solvation free energies obtained by the free energy perturbation method implemented in Monte Carlo simulations are in moderate accord with the IEF-PCM results, but consideration of the ΔGsolv/MC values in calculating ΔGstot maintains the tautomeric preferences. It was revealed from the Monte Carlo solution structure analyses that the S atom is not a hydrogen-bond acceptor in any OH-substituted thiazole or isothiazole, and the OH-substituted isoxazole and oxazole ring oxygens may act as a weak hydrogen-bond acceptor at most. The mols. form 1.0-3.4 solute-water hydrogen bonds in generally unexplored numbers at some specific solute sites. Nonetheless, hydrogen-bond formation is favorable with the NH, C=O and OH groups. This study involved multiple reactions and reactants, such as Isoxazol-4-ol (cas: 80348-66-9SDS of cas: 80348-66-9).

Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Isoxazole can be synthesised via a variety of methods. Examples include via the reaction of hydroxylamine with 1,3-diketones or derivatives of propiolic acid.SDS of cas: 80348-66-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Galenko, Ekaterina E.’s team published research in Journal of Organic Chemistry in 84 | CAS: 1076-59-1

Journal of Organic Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, SDS of cas: 1076-59-1.

Galenko, Ekaterina E. published the artcileIsoxazole Strategy for the Synthesis of α-Aminopyrrole Derivatives, SDS of cas: 1076-59-1, the publication is Journal of Organic Chemistry (2019), 84(17), 11275-11285, database is CAplus and MEDLINE.

The synthesis of Me 5-aminopyrrole-3-carboxylates from 4-methyleneisoxazol-5-ones via “cyanide Michael addition/methylation/reductive isoxazole-pyrrole transformation” is developed. The last step occurs in a domino mode involving Mo(CO)6-mediated reductive isoxazole ring-opening, Mo(CO)6-catalyzed cis-trans-isomerization of the enamine intermediate followed by 1,5-exo-dig cyclization. 5-Amino-1H-pyrrolo-3-carboxylates react with 1,3-diketones, affording pyrrolo[1,2-a]pyrimidine-7-carboxylates, and are easily converted into 2-diazo-2H-pyrrole-4-carboxylates. These compounds demonstrate the reactivity of both diazo compounds, giving pyrrole-containing products of intra/intermol. azo coupling, and carbenes to give pyrrole-containing insertion products into CH and OH bonds under photolysis.

Journal of Organic Chemistry published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, SDS of cas: 1076-59-1.

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

Kerr, William J.’s team published research in Chemical Communications (Cambridge, United Kingdom) in 52 | CAS: 2251-79-8

Chemical Communications (Cambridge, United Kingdom) 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.

Kerr, William J. published the artcileIridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C-H activation of unprotected tetrazoles, Application In Synthesis of 2251-79-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(40), 6669-6672, database is CAplus and MEDLINE.

The first examples of selective ortho-directed C-H activation with unprotected 2-aryltetrazoles I (X = 4-MeO, 2-Me, 3-Cl, etc.) are described. A new base-assisted protocol for iridium(I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, e.g., II, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.

Chemical Communications (Cambridge, United Kingdom) 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

Andersen, Jacob Lauwring’s team published research in Bioorganic & Medicinal Chemistry Letters in 27 | CAS: 1076-59-1

Bioorganic & Medicinal Chemistry Letters published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, SDS of cas: 1076-59-1.

Andersen, Jacob Lauwring published the artcileThe identification of novel acid isostere based inhibitors of the VPS10P family sorting receptor Sortilin, SDS of cas: 1076-59-1, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(11), 2629-2633, database is CAplus and MEDLINE.

Using fragment based and structure based drug discovery strategies a series of novel Sortilin inhibitors has been identified. The inhibitors are based on the N-substituted 1,2,3-triazol-4-one/ol heterocyclic template. X-ray crystallog. shows that the 1,2,3-triazol-4-one/ol acts as a carboxylic acid isostere, making a bi-dentate interaction with an arginine residue of Sortilin, an interaction which has not been previously characterized for this heterocycle.

Bioorganic & Medicinal Chemistry Letters published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C9H7NO2, SDS of cas: 1076-59-1.

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

Zhong, Xiuhua’s team published research in Organic Chemistry Frontiers in 9 | CAS: 1076-59-1

Organic Chemistry Frontiers published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C12H14O2, Computed Properties of 1076-59-1.

Zhong, Xiuhua published the artcileRh-Catalysed cascade C-H imidization/cyclization of N-methoxybenzamides with isoxazolones for the assembly of dihydroquinazolin-4(1H)-one derivatives, Computed Properties of 1076-59-1, the publication is Organic Chemistry Frontiers (2022), 9(7), 1904-1910, database is CAplus.

Using isoxazolones as viable imidizating reagents, an efficient Rh(III)-catalyzed C-H imidization/cyclization cascade was developed for the specific assembly of dihydroquinazolin-4(1H)-ones I [R = H, 7-Me, 5-Cl, etc.; R1 = Me, Et, Bn; R2 = Me, Et, Ph, etc.] with the equipment of a quaternary carbon center. This protocol featured the simultaneous formation of two novel C-N bonds in a one-pot fashion with good compatibility and practicality. Combined DFT calculations and exptl. studies clarified the tandem C-H activation/oxidation addition/C-H amination/isomerization/intramol. cyclization sequence for this transformation, in which the Rh(V) nitrenoid and the imine species might be involved as active intermediates.

Organic Chemistry Frontiers published new progress about 1076-59-1. 1076-59-1 belongs to isoxazole, auxiliary class Oxazoline,Benzene,Ester, name is 3-Phenylisoxazol-5(2H)-one, and the molecular formula is C12H14O2, Computed Properties of 1076-59-1.

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

Ciou, Yan-Syun’s team published research in Journal of Organic Chemistry in 82 | CAS: 57103-14-7

Journal of Organic Chemistry published new progress about 57103-14-7. 57103-14-7 belongs to isoxazole, auxiliary class Fused Tricycles,Carbazoles, name is 9-(4-Fluorophenyl)-9H-carbazole, and the molecular formula is C18H12FN, Product Details of C18H12FN.

Ciou, Yan-Syun published the artcileCross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D-π-A Organic Dyes: C-H/C-H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications, Product Details of C18H12FN, the publication is Journal of Organic Chemistry (2017), 82(7), 3538-3551, database is CAplus and MEDLINE.

A variety of push-pull type organic dyes are facilely synthesized through the most atom-economical C-H/C-H dehydrogenative coupling reactions. After comprehensive synthetic optimizations, a broad substrate scope is achieved and functional groups, such as ester, ketone, nitrile, nitro, and triazene are well tolerated. The sensitive aldehyde group required for the conversion into anchoring groups for DSSCs applications is also compatible under present oxidant-containing reaction conditions. Based on this optimum C-H/C-H coupling approach, three new organic sensitizers are readily prepared and submitted to solar cell device fabrications, giving the power conversion efficiency (PCE) up to 4.85%. This work constitutes the first example that connects high atom-efficiency C-H/C-H green catalysis with dye-sensitized solar cell applications.

Journal of Organic Chemistry published new progress about 57103-14-7. 57103-14-7 belongs to isoxazole, auxiliary class Fused Tricycles,Carbazoles, name is 9-(4-Fluorophenyl)-9H-carbazole, and the molecular formula is C18H12FN, Product Details of C18H12FN.

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

Li, Rong-sheng’s team published research in Guangdong Yixue in 36 | CAS: 198470-85-8

Guangdong Yixue published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C19H17N2NaO4S, COA of Formula: C19H17N2NaO4S.

Li, Rong-sheng published the artcileComparison on efficacy of different doses of butorphanol combined with preoperative parecoxib sodium for postoperative patient-controlled intravenous analgesia in female patients, COA of Formula: C19H17N2NaO4S, the publication is Guangdong Yixue (2015), 36(4), 605-607, database is CAplus.

Objective: To explore the appropriate dose of butorphanol combined with preoperative parecoxib sodium for postoperative patient-controlled i.v. analgesia. Methods: 75 Cases of ASA I-II female patients undergoing lower abdomen or lower limb operation were selected. All patients underwent operation under spinal-epidural combined anesthesia. After operation, the patients were given butorphanol 6 mg (group A, n = 25), 8 mg (group B, n = 25) and 10 mg (group C, n = 25), resp. for patient-controlled i.v. analgesia. The above-mentioned butorphanol was diluted as 100 mL with physiol. saline solution The amount of background infusion was 1.8 mL/h, and the single dose was 2 mL. The patients were i.m. injected with tramadol 100 mg for rescue analgesia. Before incision, all patients were given parecoxib sodium 40 mg. After operation, the pain visual analog score (VAS score) and Ramsay sedation score (RSS score) were observed The adverse reactions and satisfaction of patients were recorded. Results: 6, 12 and 24 h after operation, the VAS score in group B and group C was significantly lower than that in group A (P < 0.05, P < 0.01). 48 H after operation, the usage amount of butorphanol in group A, group B and group C was successively increased (P < 0.01). The incidence (24%) of dizziness in group C was higher than that (4%) in group A. The proportion (24%) of rescue analgesia in group A was higher than that (4%) in the other two groups (P < 0.05). The VAS score and RSS score in three groups had no statistically significant difference (P > 0.05). Conclusion: For the female patients undergoing lower abdomen or lower limb operation, preoperative i.v. injection of parecoxib sodium 40 mg combined with postoperative 1.8 mL/h butorphanol 8 mg is suitable for patient-controlled i.v. analgesia.

Guangdong Yixue published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C19H17N2NaO4S, COA of Formula: C19H17N2NaO4S.

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

Yao, Shao-hong’s team published research in Xiandai Zhenduan Yu Zhiliao in 28 | CAS: 198470-85-8

Xiandai Zhenduan Yu Zhiliao published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C4H5NS2, Application of Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide.

Yao, Shao-hong published the artcileEffect of parecoxib sodium in remifentanil anesthesia during hip replacement surgery on cognitive function of elderly patients, Application of Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, the publication is Xiandai Zhenduan Yu Zhiliao (2017), 28(8), 1423-1424, database is CAplus.

To explore the effect of parecoxib sodium in remifentanil anesthesia in hip replacement surgery on the cognitive function of elderly patients. We randomly selected 100 patients who received hip replacement surgery in our hospital as the research objects, and divided them into the control group and the observation group. After remifentanil anesthesia, they were given 0.9% sodium chloride solution and parecoxib sodium to compare and analyze application effects. The MMSE scores of patients in the observation group were significantly higher than those in the control group on the 1st and 7th day after surgery (P < 0.05). The Barthel index score and Harris score (89.23 ± 12.06) and (88.96 ± 12.76) points of the observation group were significantly higher than those of the control group (42.74 ± 11.46) and (45.57 ± 11.65) points (P < 0.05). The application of parecoxib sodium in remifentanil anesthesia in hip replacement surgery has a significant impact on the cognitive function of elderly patients, improves their postoperative cognitive function, has a good prognosis, is safe and reliable, and is of great significance.

Xiandai Zhenduan Yu Zhiliao published new progress about 198470-85-8. 198470-85-8 belongs to isoxazole, auxiliary class Immunology/Inflammation,COX, name is Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide, and the molecular formula is C4H5NS2, Application of Sodium ((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)(propionyl)amide.

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