M.W=150-200 | Page 6 of 11 | Heterocyclic Building Blocks-isoxazole

Loro, Camilla’s team published research in Organic Letters in 24 | CAS: 1076-59-1

Organic 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, Quality Control of 1076-59-1.

Loro, Camilla published the artcileNon-Decarboxylative Ruthenium-Catalyzed Rearrangement of 4-Alkylidene-isoxazol-5-ones to Pyrazole- and Isoxazole-4-carboxylic Acids, Quality Control of 1076-59-1, the publication is Organic Letters (2022), 24(16), 3092-3096, database is CAplus and MEDLINE.

Non-decarboxylative ruthenium-catalyzed rearrangement of 4-(2-hydroaminoalkylidenyl)- and 4-(2-hydroxyalkylidenyl)-substituted isoxazol-5(4H)-ones with catalytic amounts of [RuCl₂(p-cymene)]₂, without any additive, afforded pyrazole-4-carboxylic acids I [R¹ = Me, Pr, Ph, etc.; R² = H, Me, Et, etc.; R³ = Ph, CH₂Bn, etc.] and isoxazole-4-carboxylic acids I [R¹ = Me, Pr, Ph, etc.; R² = H, Me, Ph, etc.] resp. The presence of an intramol. H-bond in these substrates was the key to divert the classical mechanism toward a ring-opening non-decarboxylative path that was expected to generate a vinyl Ru-nitrenoid intermediate, the cyclization of which afforded the rearranged products I and II. A gram scale protocol demonstrated the synthetic applicability of this transformation.

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

Sutariya, Tushar R.’s team published research in RSC Advances in 5 | CAS: 1076-59-1

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 C9H11BO4, Quality Control of 1076-59-1.

Sutariya, Tushar R. published the artcileA domino synthetic approach for new, angular pyrazol- and isoxazol-heterocycles using [DBU][Ac] as an effective reaction medium, Quality Control of 1076-59-1, the publication is RSC Advances (2015), 5(30), 23519-23529, database is CAplus.

The synthesis of pyrazole and isoxazole based heterocycles, e.g., I and II (R = H, Cl), via domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction of O-alkenylated acetophenones with active methylene pyrazolones and 3-phenyl-1,2-oxazol-5-one, resp., in an ionic liquid [DBU][Ac], effectively at 130 °C were described. The DKHDA reaction of O-alkynylated acetophenones is also feasible with 3-phenyl-1,2-oxazol-5-one but in the presence of ZnO as catalyst because it contains the unactivated dienophile moiety. The heterosteroid-mimicking structure II (R = H, Cl) thus achieved may have different bioprofiles than the aldehyde-derived one. The use of recyclable ionic liquid in place of organic solvents in the present method offers both ecol. and environmental benefits. The stereochem. of synthesized compounds was confirmed by the single crystal X-ray diffraction data.

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

Martinez-Pardo, Pablo’s team published research in Advanced Synthesis & Catalysis in 362 | CAS: 1076-59-1

Advanced Synthesis & Catalysis 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.

Martinez-Pardo, Pablo published the artcileEnantioselective Synthesis of Functionalized Diazaspirocycles from 4-Benzylideneisoxazol-5(4H)-one Derivatives and Isocyanoacetate Esters, Recommanded Product: 3-Phenylisoxazol-5(2H)-one, the publication is Advanced Synthesis & Catalysis (2020), 362(17), 3564-3569, database is CAplus.

Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4-arylideneisoxazol-5-ones and isocyanoacetate esters using a bifunctional squaramide/Bronsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers.

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.

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.

Referemce:
https://en.wikipedia.org/wiki/Isoxazole,
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.

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

Wang, Tong-Tong’s team published research in Organic Letters in 23 | CAS: 1076-59-1

Wang, Tong-Tong published the artcileRh(III)-Catalyzed Regioselective Annulations of 3-Arylisoxazolones and 3-Aryl-1,4,2-dioxazol-5-ones with Propargyl Alcohols: Access to 4-Arylisoquinolines and 4-Arylisoquinolones, HPLC of Formula: 1076-59-1, the publication is Organic Letters (2021), 23(15), 5952-5957, database is CAplus and MEDLINE.

The Rh(III)-catalyzed dual directing group assisted C-H activation/annulation of 3-arylisoxazolones with propargyl alcs. were developed, which expanded the application scope of isoxazolones in organic synthesis. This protocol also worked well with 3-aryl-1,4,2-dioxazol-5-ones to produce synthetically and biol. important 4-arylisoquinolones.

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

Salma, Sabrina Aufar’s team published research in Molecular Crystals and Liquid Crystals in 705 | CAS: 1076-59-1

Molecular Crystals and Liquid Crystals 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.

Salma, Sabrina Aufar published the artcileSynthesis and characterization of new dyes based on chromone malononitrile as the electron withdrawing group and their photovoltaic effect, Computed Properties of 1076-59-1, the publication is Molecular Crystals and Liquid Crystals (2020), 705(1), 28-34, database is CAplus.

Two new small mol. dyes for the donor material, named IDTT-OX and IDTT-EPMP-IDC have been successfully synthesized and characterized for solution-processed bulk heterojunction organic solar cells (OSCs). These dyes are containing indacenodithieno[3,2-b]thiophene (IDTT) as the donor moiety, phenylisoxazolone (OX) and malononitrile derivatives (EPMP-IDC) as the acceptor. IDTT-OX exhibits a strong self-aggregation behavior and broad absorption with an optical band gap of 1.88 eV. While IDTT-EPMP-IDC shows different behavior, the self-aggregation of IDTT-EPMP was efficiently restricted by the presence of the alkyl group at EPMP-IDC functional group in the mol. and it has 1.60 eV optical bandgap. The inverted-type OSCs based on the blend of IDTT-OX (or IDTT-EPMP-IDC) as a donor, PC₇₁BM as an acceptor are fabricated. The power conversion efficiencies (PCEs) of the optimized OSCs are reached up to 0.29% for IDTT-OX and 2.07% for IDTT-EPMP-IDC.

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

Capreti, Naylil M. R.’s team published research in Organic Letters in 17 | CAS: 1076-59-1

Capreti, Naylil M. R. published the artcileMichael Addition of Soft Carbon Nucleophiles to Alkylidene Isoxazol-5-ones: A Divergent Entry to β-Branched Carbonyl Compounds, Application of 3-Phenylisoxazol-5(2H)-one, the publication is Organic Letters (2015), 17(10), 2490-2493, database is CAplus and MEDLINE.

A novel, divergent strategy toward the synthesis of β-branched (and linear) carbonyl compounds is developed by taking advantage of alkylidene isoxazol-5-ones as key building blocks. The yields obtained range from good to excellent, therefore making the described methods attractive options for building such mols. E.g., reaction of alkylidene isoxazol-5-one (I) with TMSOCPh:CH₂, catalyzed by Sc(OTf)₃, gave 90% II. Treatment of II with Fe(SO₄) and NaNO₂ gave 83% PhCCCHPhCH₂COPh.

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

Krasnaya, Zhanna A.’s team published research in Mendeleev Communications in 24 | CAS: 1076-59-1

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 C9H7NO2, Synthetic Route of 1076-59-1.

Krasnaya, Zhanna A. published the artcileSynthesis and conformations of cross-conjugated polyenes containing heterocyclic moieties with diverse structures, Synthetic Route of 1076-59-1, the publication is Mendeleev Communications (2014), 24(6), 377-379, database is CAplus.

New non-linear cross-conjugated polyenes containing a central 4-ylidene-substituted pyran or N-methyldihydropyridine ring were synthesized. Interaction of chromophores in these compounds occurs through the ylidene group linked to the heterocycles.

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