Tag: M.W=150-200

Griesbeck, Axel G. published the artcilePhotocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: cycloaddition reactivity and stability studies, Computed Properties of 1076-59-1, the publication is Beilstein Journal of Organic Chemistry (2011), 127-134, database is CAplus and MEDLINE.

The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. E.g., photocycloaddn of 3,4,5-trimethylisoxazole with PhCHO gave 50% exo-oxetane I. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes, e.g. I, were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole-derived oxetanes show type T photochromism.

Beilstein 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, Computed Properties of 1076-59-1.

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

Hellmuth, Tina published the artcileRegioselective Catalytic Asymmetric C-Alkylation of Isoxazolinones by a Base-Free Palladacycle-Catalyzed Direct 1,4-Addition, Recommanded Product: 3-Phenylisoxazol-5(2H)-one, the publication is Angewandte Chemie, International Edition (2015), 54(9), 2788-2791, database is CAplus and MEDLINE.

Herein the first catalytic asym. alkylations of isoxazolinones I [R¹ = Me, n-Pr, Ph, PhCH₂, 2-naphthylmethyl, etc.; R² = Me, Ph, 4-O₂NC₆H₄, etc.; R¹R² = (CH₂)₄] with vinyl ketones R³C(O)CH:CH₂ (R³ = Me, Et, Ph, 4-MeOC₆H₄, PhCH₂CH₂) forming isoxazolones II with all-C-substituted quaternary stereocenter are reported. The present studies were driven by the question of how to control the regioselectivity in the competition of various nucleophilic positions. The investigation of a direct 1,4-addition uncovered that a sterically demanding palladacycle catalyst directs the reactivity in the absence of a base nearly exclusively to the nucleophilic C atom, while at the same time it allows for high enantioselectivity and TONs up to 1900.

Angewandte Chemie, International Edition 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

Galenko, Ekaterina E. published the artcileDomino transformation of isoxazoles to 2,4-dicarbonylpyrroles under Fe/Ni relay catalysis, Synthetic Route of 1076-59-1, the publication is RSC Advances (2015), 5(24), 18172-18176, database is CAplus.

The domino reaction of 5-alkoxy- or 5-aminoisoxazoles, under metal relay catalysis, with sym. 1,3-diketones gives 4-acylpyrrole-2-carboxylic acid derivatives in high yield. Esters and amides of acylacetic acids reacted regioselectively, giving derivatives of pyrrole-2,4-dicarboxylic acid as the main products.

RSC Advances 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, Synthetic Route of 1076-59-1.

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

Serebryannikova, Anna V. published the artcileSynthesis of Isoxazole- and Oxazole-4-carboxylic Acids Derivatives by Controlled Isoxazole-Azirine-Isoxazole/Oxazole Isomerization, SDS of cas: 1076-59-1, the publication is Journal of Organic Chemistry (2019), 84(23), 15567-15577, database is CAplus and MEDLINE.

The first synthesis of isoxazole-4-carboxylic acid derivatives by domino isoxazole-isoxazole isomerization is reported. Fe(II)-catalyzed isomerization of 4-acyl-5-methoxy-/5-aminoisoxazoles (dioxane, 105°) leads to the formation of isoxazole-4-carboxylic esters and amides in good yields. 4-Formyl-5-methoxyisoxazoles give Me oxazole-4-carboxylates under the same reaction conditions. Fe(II)-catalyzed isomerization of 4-acyl-5-methoxyisoxazoles under milder conditions (MeCN, 50°) allows the preparation of transient 2-acyl-2-(methoxycarbonyl)-2H-azirines. The azirines isomerize quant. either into isoxazoles under catalytic conditions (dioxane, 105°) or into oxazoles under noncatalytic thermolysis (o-dichlorobenzene, 170°). The mechanism of the isomerization and dependence of the reaction routes on substituents at starting isoxazole core and reaction conditions are discussed on the basis of DFT calculations

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 C22H18O2, SDS of cas: 1076-59-1.

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

Altieri, Elisa published the artcileAn improved diastereoselective synthesis of spiroazoles using multi-component domino transformations, Formula: C9H7NO2, the publication is Synlett (2010), 2106-2108, database is CAplus.

Spiroisoxazole and spiropyrazole derivatives were obtained in a four-component reaction of active isoxazol- or pyrazol-5-ones with aromatic aldehydes, phenacyl chloride and AcOH-AcONH₄ mixture The reaction sequence is highly chemo- and diastereoselective affording good yields of spiroisoxazoles in refluxing ethanol, while efficient formation of spiropyrazoles is closely related to the use of a microwave-assisted protocol.

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 C9H7NO2, Formula: C9H7NO2.

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

Fernandes, Alessandra A. G. published the artcileGeneral Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies, Formula: C9H7NO2, the publication is European Journal of Organic Chemistry (2019), 2019(19), 3022-3034, database is CAplus.

A general platform for the conversion of isoxazol-5-ones to 3,5-disubstituted isoxazoles has been developed via a two-step strategy. The first step leads to the formation of 5-(pseudo)halogenated isoxazoles, while in the second, a variety of heteroalkyl-, heteroaryl-, alkyl-, alkenyl-, alkynyl- and aryl-chains can be installed via nucleophilic substitutions or palladium catalyzed cross-coupling reactions.

European 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, Formula: C9H7NO2.

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

Begue, Didier published the artcileNitrile Imines and Nitrile Ylides: Rearrangements of Benzonitrile N-Methylimine and Benzonitrile Dimethylmethylide to Azabutadienes, Carbodiimides, and Ketenimines. Chemical Activation in Thermolysis of Azirenes, Tetrazoles, Oxazolones, Isoxazolones, and Oxadiazolones, Application In Synthesis of 1076-59-1, the publication is Journal of Organic Chemistry (2014), 79(3), 1247-1253, database is CAplus and MEDLINE.

Flash vacuum thermolysis (FVT) of 1-methyl-5-phenyltetrazole (5b), 2-methyl-5-phenyltetrazole (1b), and 3-methyl-5-phenyl-1,3,4-oxadiazol-2-(3H)-one (3b) affords the nitrile imine (2b), which rearranges in part to N-methyl-N’-phenylcarbodiimide (7b). Another part of 2b undergoes a 1,4-H shift to the diazabutadiene (13). 13 undergoes two chem. activated decompositions, to benzonitrile and CH₂NH and to styrene and N₂. FVT of 2,2-dimethyl-4-phenyl-oxazol-5-(2H)-one (16) at 400 °C yields 3-methyl-1-phenyl-2-azabutadiene (18) in high yield. In contrast, FVT of 3,3-dimethyl-2-phenyl-1-azirene (21) at 600 °C or 4,4-dimethyl-3-phenyl-isoxazolone (20) at 600 °C affords only a low yield of azabutadiene (18) due to chem. activated decomposition of 18 to styrene and acetonitrile. There are two reaction paths from azirene (21): one (path a) leading to nitrile ylide (17) and the major products styrene and acetonitrile and the other (path b) leading to the vinylnitrene (22) and ketenimine (23). The nitrile ylide PhC^–N⁺C-(CH₃)₂ (17) is implicated as the immediate precursor of azabutadiene (18). FVT of either 3-phenylisoxazol-5-(4H)-one (25) or 2-phenylazirene (26) at 600 °C affords N-phenylketenimine (28). The nitrile ylide PhC^–N⁺CH₂ (30) is postulated as a reversibly formed intermediate. N-Phenylketenimine (28) undergoes chem. activated free radical rearrangement to benzyl cyanide. The mechanistic interpretations are supported by calculations of the energies of key intermediates and transition states.

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, Application In Synthesis of 1076-59-1.

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

Poe, Ambata published the artcileEffective tuning of ketocyanine derivatives through acceptor substitution, Category: isoxazole, the publication is Chemistry – A European Journal (2015), 21(21), 7721-7725, database is CAplus and MEDLINE.

A series of ketocyanine derivatives possessing bis(diarylamino)fluorenyl donors and variable acceptors installed at the bridging carbon atom were synthesized to investigate how the electronic structure of the dye can be systemically tuned through stabilization of the cyanine-like character of the donor by increasing the acceptor strength. Anal. of the ¹H NMR spectra indicates that the “charge-separated” species dominates in these dyes, given that carbons possessing a pos. or neg. charge in the resonance structures of this state purposefully shift downfield or upfield, resp., depending on the strength of the acceptor moiety. In DAA-Fl-PI, (a fluorenylideneisoxazolone) the acceptor strength and the gain of acceptor aromaticity indicates a predisposition of the separated state, indicated by asymmetry in the ¹H NMR spectrum, as well as uneven distribution of the HOMO on the fluorenyl donor.

Chemistry – A European Journal 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

De Castro, Pedro P. published the artcileQuantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones, Application of 3-Phenylisoxazol-5(2H)-one, the publication is Journal of Organic Chemistry (2019), 84(19), 12573-12582, database is CAplus and MEDLINE.

The theor.-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first exptl. report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen- or carbon-acyloxy adducts.

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, Application of 3-Phenylisoxazol-5(2H)-one.

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