Day: November 21, 2022

Jana, Sripati published the artcileC-H Functionalization Reactions of Unprotected N-Heterocycles by Gold-Catalyzed Carbene Transfer, Recommanded Product: 9-(4-Fluorophenyl)-9H-carbazole, the publication is ACS Catalysis (2020), 10(17), 9925-9931, database is CAplus.

The C-H functionalization reaction of N-heterocycles with an unprotected N-H group is one of the most step-economic strategies to introduce functional groups without the need for installation and removal of protecting groups. Despite recent significant advances in C-H functionalization chem., this strategy remains unsatisfactorily developed. In this report, we disclose a simple and straightforward protocol to allow for the selective C-H functionalization of unprotected double-benzannellated N-heterocycles via gold-catalyzed carbene-transfer reactions (29 examples, up to 86% yield). The scope of the reaction can also be expanded to the corresponding protected heterocycles (37 examples, up to 98% yield), further demonstrating the generality of this method. Mechanistic studies by d. functional theory (DFT) calculations underpin the importance of the gold catalyst and reveal that the selectivity of this reaction is driven by trace amounts of water present in the reaction mixture

ACS Catalysis 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, Recommanded Product: 9-(4-Fluorophenyl)-9H-carbazole.

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

Fadda, Ahmed A. published the artcileSynthesis, characterization, antioxidant and antitumor evaluation of new phthalocyanines containing peripherally functionalized fused heterocyclic compounds, Recommanded Product: 3-Phenylisoxazol-5(2H)-one, the publication is Dyes and Pigments (2018), 300-312, database is CAplus.

The synthesis of novel phthalocyanines with various functional groups and/or heterocycles at peripheral and axial positions via the reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 1,4-diazabicyclo[2.2.2]octane (DBO) was reported. Also, reaction of modified phthalonitrile derivatives with hydroquinone or DDQ afforded the corresponding new phthalocyanine derivatives Moreover, a new generation of phthalocyanine derivatives were synthesized by cyclotetramerization of phthalic anhydride derivatives in the presence of 1,3-divinyl-1,1,3,3-tetramethyldisilazane as catalyst. The structures of newly synthesized compounds were established by both elemental and spectral analyses. The antioxidant activity of the products was screened in series of in-vitro tests. In addition, the toxicity of the synthesized compounds was studied at four different cell lines HepG2, WI-38, Vero and MCF-7 cell lines. According to the results, compounds I and II showed very strong activity against all cell lines and act as good antioxidant agents.

Dyes and Pigments 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, Recommanded Product: 3-Phenylisoxazol-5(2H)-one.

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

Vereshchagin, Anatoly N. published the artcilePot, atom and step economic (PASE) synthesis of 5-isoxazolyl-5H-chromeno[2,3-b]pyridine scaffold, Quality Control of 1076-59-1, the publication is Mendeleev Communications (2015), 25(6), 424-426, database is CAplus.

The new multicomponent reaction of salicylaldehydes, e.g., I, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and 3-phenylisoxazol-5(4H)-one gave the corresponding substituted 2,4-diamino-5-(5-oxo-3-aryl-2,5-dihydroisoxazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles, e.g., II, which are promising for biomedical applications.

Mendeleev Communications 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 C8H11BO2S, Quality Control of 1076-59-1.

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

Vereshchagin, Anatoly N. published the artcileStereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones, Computed Properties of 1076-59-1, the publication is Synlett (2016), 27(17), 2489-2493, database is CAplus.

The new chem. cascade reaction was found: the direct formation of substituted 4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles from benzylidenemalononitriles and 3-aryl-2-isoxazol-5(4H)-ones. The action of bromine on the equimolar mixture of benzylidenemalononitrile and 3-aryl-2-isoxazol-5(4H)-one in the basic alc. solution results in stereoselective formation of spirobicycle containing the 2-isoxazolin-5-one and the cyclopropane fragments in 53-92% yields. Thus, the new simple and efficient ‘one-pot’ approach to substituted (2R*,3R*)-4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles was found directly from simple and reasonable starting compounds as benzylidenemalonitriles and 3-aryl-2-isoxazol-5(4H)-ones.

Synlett 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 C9H6N2O2, Computed Properties of 1076-59-1.

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

Vereshchagin, Anatoly N. published the artcileHighly diastereoselective amine-catalyzed Knoevenagel-Michael cyclization-ring opening cascade between aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones, Name: 3-Phenylisoxazol-5(2H)-one, the publication is Molecular Diversity (2018), 22(3), 627-636, database is CAplus and MEDLINE.

A highly diastereoselective three-component cascade reaction among aromatic aldehydes R¹CHO (R¹ = Ph, 4-ClC₆H₄, 4-O₂NC₆H₄, 4-MeC₆H₄, 4-MeOC₆H₄), 3-arylisoxazol-5(4H)-ones (aryl = R² = Ph, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄) and 3-aminocyclohex-2-en-1-ones I (R³ = H, Me; R⁴ = H, PhCH₂) took place under the catalysis with triethylamine to provide the corresponding hydroxyimino-functionalized tetrahydroquinolinediones II in 45-85% yields. The transformation presumably proceeds through a sequential cascade of Knoevenagel/Michael addition/cyclization/ring opening reactions. This process was carried out in green media (EtOH/water, 1:1-1:3) at reflux. Products were crystallized directly from the reaction mixture and their isolation includes only filtration. The structure of tetrahydroquinolinedione I (R¹ = R² = Ph; R³ = Me; R⁴ = H) was confirmed by X-ray diffraction anal.

Molecular Diversity 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 C10H12F6N4O6PdS2, Name: 3-Phenylisoxazol-5(2H)-one.

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

Sharghi, Hashem published the artcileFacile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H-tetrazoles catalyzed by recyclable 4′-phenyl-2,2′:6′,2”-terpyridine copper(II) complex immobilized onto activated multi-walled carbon nanotubes, Formula: C8H5F3N4, the publication is Journal of Organometallic Chemistry (2013), 41-48, database is CAplus.

A phenylterpyridine copper complex immobilized on oxidized multiwalled carbon nanotubes (MWCNT) was prepared and characterized; the MWCNT-supported terpyridine copper complex was used as a catalyst for the reaction of sodium azide with electron-rich and electron-poor aryl nitriles to give 5-aryltetrazoles in 75-98% yields and for the reaction of sodium azide, tri-Et orthoformate, and electron-rich and electron-poor arylamines to give 1-aryltetrazoles in 80-95% yields. The reaction of 4-methylbenzonitrile and sodium azide to give 5-(4-methylphenyl)tetrazole was repeated four times using the same catalyst, with product formed in 85-90% yields.

Journal of Organometallic 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 C7H8O3, Formula: C8H5F3N4.

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

Reddy, Koduru Janardhan published the artcileSeparation studies of Pd(II) from acidic chloride solutions of Pt(IV), Ni(II) and Rh(III) by using 4-aroyl-3-phenyl-5-isoxazolones, Category: isoxazole, the publication is Journal of Chemistry (2012), 9(2), 756-765, database is CAplus.

This study examined the effect influence of various factors on the extraction of Pd(II) to develop a new liquid-liquid extraction mechanism for the selective separation of palladium(II) from its acidic chloride solutions using 4-aroyl-3-phenyl-5-isoxazolones (HA), such as 3-phenyl-4-(4-fluorobenzoyl)-5-isoxazolone (HFBPI), 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and 3-phenyl-4-(4-toluoyl)-5-isoxazolone (HTPI). The extraction strength of Pd(II) with HA were in the following order: HFBPI > HPBI > HTPI, which is opposite to that observed with their pK_a values. HPBI was used to sep. Pd(II) from Pt(IV), Ni(II) and Rh(III) metal ions and calculated their separation factors (S.F.) were followed in the order: Pd/Ni (40 ± 0.4) > Pd/Pt (25 ± 0.2) > Pd/Rh (15 ± 0.3) > Rh/Ni (2.7 ± 0.3) > Pt/Ni â‰?Rh/Pt (1.7 ± 0.2). The loading and striping of Pd(II) (1.12 × 10^-4 mol L^-1) were also examined using 1.0 × 10^-3 mol L^-1 HPBI in CHCl₃ and 1.0 mol L^-1 HCl, resp. The results demonstrated that the maximum (97.5%) extraction and desorption (89%) of metal required at least 3.0 cycles. The developed method was applied successfully to the separation of palladium from synthetic water samples.

Journal of 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, Category: isoxazole.

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

Feinn, Liana published the artcileAntimicrobial Evaluation of 5-Substituted Aryl 1H-Tetrazoles, COA of Formula: C8H5F3N4, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2017), 13(4), 359-364, database is CAplus.

Tetrazole derivatives such as 1-substituted dinitrobenzyl tetrazoles and their oxa and selanyl analogs have previously been studied against drug-susceptible and multidrug-resistant mycobacteria. In addition, other tetrazole derivatives have been shown to inhibit CTX-M class A β-lactamases. We studied the antibacterial activity of 5-substituted aryl 1H-tetrazole derivatives The antibacterial activity of several known 5-substituted aryl 1H-tetrazole derivatives was evaluated against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. The activity was assessed by determining the min. inhibitory concentration of these tetrazole derivatives and comparing them to the known antibiotics amoxicillin, trimethoprim, and sulfamethoxazole. Some derivatives showed significant antibacterial activity with the most active derivatives exhibiting a min. inhibitory concentration (MIC) of 125-250 μg/mL against S. aureus and E. coli. Using some of these tetrazole compounds in combination with trimethoprim led to a synergistic effect that gave MIC values ranging from 0.24-1.95 μg/mL against E. coli and 3.91-31.3 μg/mL against S. aureus. The tetrazole derivatives were prepared in an isopropanol/water mixture using microwave heating at 160° for 1 h. The cycloaddition between organonitriles and sodium azide was catalyzed by indium chloride. This study shows a significant synergistic effect between the tetrazole compounds tested and trimethoprim which could be used to potentially develop new antibacterial agents.

Medicinal Chemistry (Sharjah, United Arab Emirates) 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, COA of Formula: C8H5F3N4.

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

Konkala, Veera Swamy published the artcileOne-pot Synthesis of 3-phenyl-4-pyrazolylmethylene-isoxazol-(5H)-ones Catalyzed by Sodium Benzoate in Aqueous Media under the Influence of Ultrasound Waves: A Green Chemistry Approach, Quality Control of 1076-59-1, the publication is Journal of Heterocyclic Chemistry (2017), 54(4), 2483-2492, database is CAplus.

A series of 4-pyrazolylmethylene-3-phenylisoxazol-5(4H)-ones have been prepared from Knoevenagel condensation of pyrazole-4-carbaxaldehyde with isoxazolone precursors (e.g., 1,3-diphenylpyrazole-4-carboxaldehyde + isoxazolone I â†?II) or via one-pot three-component cyclocondensation of pyrazole-4-carbaxaldehyde with β-ketoesters and hydroxylamine hydrochloride (e.g., 1,3-diphenylpyrazole-4-carboxaldehyde + Et benzoylacetate + hydroxylamine hydrochloride â†?II) in the presence of sodium benzoate in water under the influence of ultrasonic waves. The merits of this method are efficient, clean, green, easy work-up, high yields, and shorter reaction time, and the catalyst could be recycled easily without affecting the catalytic activity.

Journal of Heterocyclic 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, Quality Control of 1076-59-1.

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

Stivanin, Mateus L. published the artcileAn Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights, Synthetic Route of 1076-59-1, the publication is Journal of Organic Chemistry (2017), 82(19), 10319-10330, database is CAplus and MEDLINE.

A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines, e.g., I (X-rays single crystal structure shown), is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.

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 C8H14O4, Synthetic Route of 1076-59-1.

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