72705-83-0

Upstream product

• 36298-61-0 3-phenyl-4-benzylideneisoxazol-5(4H)-one 
• 56409-75-7 ethyl 2-benzyl-3-oxo-3-phenylpropanoate 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 100-52-7 benzaldehyde 
• 121-44-8 triethylamine 
• 1088-32-0 3-phenyl-4-(1-phenylmethylidene)-5-isoxazolone 

Relevant academic research and scientific papers

Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles: An efficient access to trisubstituted isoxazoles

The Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles 1 at the C5 position has successfully proceeded in the presence of Pd2(dba)3 and P(t-Bu)3·HBF4 catalysts to give the corresponding trisubstituted isoxazoles 3 in good to high yields while suppressing the formation of ketone 4 as a byproduct. The use of bulky phosphine ligand P(t-Bu)3·HBF4 is essential for the current transformation, and the formation of ketone 4, which was a major product in the previous report, was able to be suppressed under the current conditions.

Complementing Pyridine-2,6-bis(oxazoline) with Cyclometalated N-Heterocyclic Carbene for Asymmetric Ruthenium Catalysis

A strategy for expanding the utility of chiral pyridine-2,6-bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N-heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chemistry, including ring contraction to chiral 2H-azirines (up to 97 % ee with 2000 TON) and enantioselective C(sp3)?H aminations (up to 97 % ee with 50 TON).

Quantum chemical-guided steglich rearrangement of azlactones and isoxazolones

The theoretical-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 experimental report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen- or carbon-acyloxy adducts.

Double Regioselective Asymmetric C-Allylation of Isoxazolinones: Iridium-Catalyzed N-Allylation Followed by an Aza-Cope Rearrangement

Isoxazolinones are biologically and synthetically interesting densely functionalized heterocycles, which for a long time were not accessible in enantioenriched form by asymmetric catalysis. Next to the deficit of enantioselective methods, the functionaliz

Asymmetric Synthesis of 2H-Azirines with a Tetrasubstituted Stereocenter by Enantioselective Ring Contraction of Isoxazoles

Highly strained 2H-azirines with a tetrasubstituted stereocenter were synthesized by the enantioselective isomerization of isoxazoles with a chiral diene–rhodium catalyst system. The effect of ligands and the coordination behavior support the proposed cat

Regioselective catalytic asymmetric C-alkylation of isoxazolinones by a base-free palladacycle-catalyzed direct 1,4-addition

Isoxazolinones constitute a class of heterocycles utilized for the development of novel drug candidates. The cyclic oxime ester motif is also synthetically useful as it contains functional handles which have previously been used to provide access to an assortment of valuable compound classes not easily accessible by alternative approaches. However, asymmetric methods towards isoxazolinones are notoriously scarce. Herein we report the first catalytic asymmetric alkylations of isoxazolinones forming all-C-substituted quaternary stereocenters. The present studies were driven by the question of how to control the regioselectivity in the competition of different 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.

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes

A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl 2]2 - NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C - H vinylation via ortho-rhodation and C - N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N - O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

4-Arylmethylisoxazol-5-one derivatives - Novel synthesis, structural studies, and supramolecular self-assembly through resonance-assisted hydrogen bonding

Arylmethylisoxazol-5-ones (3) were prepared by a new mild reductive procedure using tertiary amines containing a flexible N-CH-CH grouping. A concurrent process competed with the reduction, yielding fair quantities of chain-elongation products (4). The X-ray structures of two selected arylmethyl derivatives are reported and are shown to have the expected different tautomeric arrangements. The unusual features of the NH-tautomer (3e) were interpreted in terms of the RAHB (resonance-assisted hydrogen bond) model and its relative stability was investigated by ab initio and DFT calculations.

C,C- and C,N-linked dimers and 4-arylmethyl derivatives from 4-arylmethylene pyrazol-5-ones and isoxazol-5-ones with 2-arylbenzimidazolines

2-Arylbenzimidazolines (8), generated in situ from o-phenylenediamine (7) and the appropriate arylaldehydes, by reaction with 4-arylmethylene pyrazol-5-ones (1) or isoxazol-5-ones (2) produce the 4-arylmethyl derivatives (3) or (4) and the C,C- (5) or the C,N-linked dimers. The reaction was rationalised on the basis of the role of 2-arylbenzimidazoline as a reducing agent and proceeds by a non-chain, free radical process involving one-electron transfer.

3,4-Disubstituted Isoxazolin-5-ones by Sodium Borohydride Reduction of 4-Arylmethylene- and 4-Alkylideneisoxazol-5(4H)-ones

Reduction of 4-arylmethylene- and 4-alkylidenisoxazol-5(4H)-ones with sodium borohydride affords the corresponding 3,4-disubstituted isoxazol-5(4H)-ones.