Heterocyclic Building Blocks-Oxazolidine

Cantalejo, Maria J. published the artcileAnalysis of Volatile Components Derived from Raw and Roasted Earth-Almond (Cyperus esculentus L.), Quality Control of 20662-83-3, the publication is Journal of Agricultural and Food Chemistry (1997), 45(5), 1853-1860, database is CAplus.

Volatile aroma components of raw earth almond and those developed in a roasting process were analyzed by gas chromatog./mass spectrometry to determine the identity of compounds that would indicate the degree of roasting. In all, 143 components (ca. 90% of the total isolate) were pos. identified, of which 138 are reported as earth almond volatiles for the 1st time. The main flavor compounds identified in raw earth almond were alcs., whereas in roasted earth almond, the majority of the volatiles identified suggest the flavor formation is via the Maillard reaction, with pyrazines contributing directly to the roasted flavor of earth almond.

Journal of Agricultural and Food Chemistry published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Quality Control of 20662-83-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Melot, Romain published the artcilePalladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C-H Bonds, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Angewandte Chemie, International Edition (2021), 60(13), 7245-7250, database is CAplus and MEDLINE.

The enantioselective functionalization of nonactivated enantiotopic secondary C-H bonds is one of the greatest challenges in transition-metal-catalyzed C-H activation proceeding by an inner-sphere mechanism. Such reactions have remained elusive within the realm of Pd⁰ catalysis. Reported here is the unique reactivity profile of the IBiox ligand family in the Pd⁰-catalyzed intramol. arylation of such nonactivated secondary C-H bonds. Chiral C₂-sym. IBiox ligands led to high enantioselectivities for a broad range of valuable indane products containing a tertiary stereocenter, as well as the arylation of secondary C-H bonds adjacent to amides. Depending on the amide substituents and upon control of reaction time, indanes containing labile tertiary stereocenters were also obtained with high enantioselectivities. Anal. of the steric maps of the IBiox ligands indicated that the level of enantioselectivity correlates with the difference between the two most occupied and the two less occupied space quadrants, and provided a blueprint for the design of even more efficient ligands.

Angewandte Chemie, International Edition published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Golovnya, R. V. published the artcileRetentions of alkyloxazoles and alkylthiazoles and their prediction based on non-linear additivity concepts in gas chromatography, Name: 4,5-Dimethyloxazole, the publication is Journal of Chromatography (1991), 552(1-2), 1-12, database is CAplus.

The gas chromatog. (GC) behavior of 39 alkyloxazoles and alkylthiazoles was studied on three capillary columns with OV-101-KF, Triton X-305-KF and PEG-40M-KF. The regularities in the thermodn. characteristics of sorption of azoles having O or S atoms were established. Energy contributions of Me, Et and Pr groups to the partial molar free energy of sorption of alkyloxazoles and alkylthiazoles were determined It was found that the contributions of the same alkyl group are different and dependent on the nature of the heterocycle and the position of the alkyl group with respect to the heteroatoms in the azole ring. Two methods for the prediction of retention indexes on the basis of the analogy of the GC behavior of azoles and inconstancy of the contributions of the same alkyl groups are given. The predicted retention indexes are in good agreement with the exptl. values.

Journal of Chromatography published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C5H7NO, Name: 4,5-Dimethyloxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Yur’ev, Yu. K. published the artcileCatalytic transformations of heterocyclic compounds. LIII. Transformations of homologs of oxazole into homologs of thiazole, Recommanded Product: 4,5-Dimethyloxazole, the publication is Zhurnal Obshchei Khimii (1958), 7-11, database is CAplus.

cf. C.A. 46, 8086a; 51, 2720d. Passage of 9 g. 2,5-dimethyloxazole (b. 115-17°, n²¹_D 1.4394, d₂₁ 0.9856) over Al₂O₃ in H₂S stream at 350° gave 13% unchanged material and 13% 2,5-dimethylthiazole, b₇₆₀ 151-3°, 1.4898, 1.0280 (picrate, m. 172°). At 300° the yield is 13%, at 375° it is 12%. At 375° 4,5-dimethyloxazole (b₇₅₅ 115-17°, n²⁰_D 1.4432, d₂₀ 0.9966) passed over Al₂O₃ in H₂S stream gave 15.5% 4,5-dimethylthiazole, b₄₇ 75-7°, 1.5193, 1.0699 (picrate, m. 187°). Similarly at 375° 2,4-dimethyloxazole (b₇₅₀ 106-8°, 1.4389, 0.9757) gave 12% 2,4-dimethylthiazole, b₅₀ 67-8°, 1.5095, 1.0513 (picrate, m. 137-8°), while 2,4,5-trimethyloxazole (b₇₆₀ 137-8°, 1.4425, 0.9569) gave similarly 10% 2,4,5-trimethylthiazole, b₂₀ 64-6°, 1.5023, 1.0327 (picrate, m. 132°). The results indicate that the oxazole ring is more stable to attack by H₂S than is furan.

Zhurnal Obshchei Khimii published new progress about 20662-83-3. 20662-83-3 belongs to oxazolidine, auxiliary class Oxazole, name is 4,5-Dimethyloxazole, and the molecular formula is C18H28N2O7, Recommanded Product: 4,5-Dimethyloxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Zhao, Lei published the artcileLigand-Controlled NiH-Catalyzed Regiodivergent Chain-Walking Hydroalkylation of Alkenes, Name: (4S,4’S)-2,2′-(Cyclohexane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole), the publication is Angewandte Chemie, International Edition (2022), 61(30), e202204716, database is CAplus and MEDLINE.

A NiH-catalyzed migratory hydroalkylation of alkenyl amines with predictable and switchable regioselectivity is reported. By utilizing a ligand-controlled, directing group-assisted strategy, various alkyl units are site-selectively installed at inert sp³ C-H sites far away from the original C=C bonds. A range of structurally diverse α- and β-branched protected amines are conveniently synthesized via stabilization of 5- and 6-membered nickelacycles resp. This method exhibits broad scope and high functional group tolerance, and can be applied to late-stage modification of medicinally relevant mols.

Angewandte Chemie, International Edition published new progress about 2185014-88-2. 2185014-88-2 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-2,2′-(Cyclohexane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole), and the molecular formula is C28H18O4, Name: (4S,4’S)-2,2′-(Cyclohexane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole).

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Li, Bijin published the artcileDual-emissive 2-(2′-hydroxyphenyl)oxazoles for high performance organic electroluminescent devices: discovery of a new equilibrium of excited state intramolecular proton transfer with a reverse intersystem crossing process, Safety of 5-(4-Bromophenyl)oxazole, the publication is Chemical Science (2018), 9(5), 1213-1220, database is CAplus and MEDLINE.

The photoluminescence (PL) and electroluminescence (EL) properties of two highly efficient excited state intramol. proton transfer (ESIPT) mols., 2-(2′-hydroxyphenyl)oxazoles containing one triphenylamine (TPA) (1) and two TPAs (2) resp., are studied systematically. The enol-forms of both 1 and 2 possess highly hybridized local and charge transfer (HLCT) excited state character, while their excited-state keto-forms are not of obvious HLCT character. A 1-based device exhibits green-white electroluminescence with Commission Internationale de l’Eclairage (CIE) coordinates of (0.25, 0.41) and a high external quantum efficiency (EQE) up to 5.3%, which is the highest EQE value recorded for single mol. white light-emitting materials. A 2-based device shows sky-blue emission with CIE coordinates of (0.18, 0.16) and an EQE of 8.0%, which is the highest EQE in the reported HLCT materials. The fluorescence intensities of the enol-forms of 1 and 2 in EL spectra are increased remarkably relative to their PL spectra. Exptl. data and theor. calculations reveal a new ESIPT equilibrium with a reverse intersystem crossing (RISC) process arising from the HLCT character. In EL, the RISC of the enol-form excitons from the triplet state to the singlet state triggers an increase in the number of enol-form singlet excitons, which further leads to a shift of the ESIPT equilibrium towards an enhanced enol-form emission. Thus, the difference between the ESIPT equilibrium in PL and EL may be ascribed to the HLCT character of the enol-form excited state.

Chemical Science published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Safety of 5-(4-Bromophenyl)oxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Chen, Peng published the artcileDiscovery of novel, potent, isosteviol-based antithrombotic agents, Recommanded Product: 5-(4-Bromophenyl)oxazole, the publication is European Journal of Medicinal Chemistry (2019), 111722, database is CAplus and MEDLINE.

Thrombosis is a pathol. coagulation process and can lead to many serious thrombotic diseases. Here, we report a novel potent antithrombotic compound (6k) based on isosteviol with anticoagulant and antiplatelet activities. 6k selectively inhibited FXa (K_i = 0.015μM) against a panel of serine proteases and showed excellent anticoagulant activity (significant prolongation of ex vivo PT and aPTT over the vehicle, p < 0.01). 6k also significantly inhibited ADP-induced platelet aggregation in rats relative to the vehicle (p < 0.01). Furthermore, 6k exhibited potent ex vivo and in vivo antithrombotic activity in rats relative to the vehicle (p < 0.01 and p < 0.0001, resp.). Novel structure 6k, with potent antithrombotic activity, is expected to lead a promising approach for the development of antithrombotic agents.

European Journal of Medicinal Chemistry published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Recommanded Product: 5-(4-Bromophenyl)oxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Yang, Ke published the artcileNickel-catalyzed decarboxylative acylation of heteroarenes by sp² C-H functionalization, Category: oxazolidine, the publication is Chemistry – A European Journal (2014), 20(24), 7241-7244, database is CAplus and MEDLINE.

Nickel-catalyzed ligand-free decarboxylative cross-coupling of azole derivatives with α-oxoglyoxylic acids was developed. This work represents the first example of decarboxylative cross-coupling reactions, in a C-H bond functionalization manner, through nickel catalysis, and tolerates various functional groups. Addnl., this approach provides an efficient access to (ox)azole ketones, an important structural motif in many medicinal compounds with a broad range of biol. activities. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemistry – A European Journal published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C8H7NO4, Category: oxazolidine.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Fullam, Elizabeth published the artcilePhysicochemical properties and Mycobacterium tuberculosis transporters: keys to efficacious antitubercular drugs?, Product Details of C14H17FN4O3, the publication is RSC Medicinal Chemistry (2021), 12(1), 43-56, database is CAplus and MEDLINE.

A review. Securing novel, safe, and effective medicines to treat Mycobacterium tuberculosis remains an elusive goal, particularly influenced by the largely impervious Mtb envelope that limits exposure and thus efficacy of inhibitors at their cellular and periplasmic targets. The impact of physicochem. properties on pharmacokinetic parameters that govern oral absorption and exposure at sites of infection is considered alongside how these properties influence penetration of the Mtb envelope, with the likely influence of transporter proteins. The findings are discussed to benchmark current drugs and the emerging pipeline, while considering tactics for future rational and targeted design strategies, based around emerging data on Mtb transporters and their structures and functions.

RSC Medicinal Chemistry published new progress about 1219707-39-7. 1219707-39-7 belongs to oxazolidine, auxiliary class Other Aliphatic Heterocyclic,Oxazolidine,Chiral,Fluoride,Benzene,Amide,Alcohol,Anti-infection, name is (R)-3-(3-Fluoro-4-(1-methyl-5,6-dihydro-1,2,4-triazin-4(1H)-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one, and the molecular formula is C14H17FN4O3, Product Details of C14H17FN4O3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Ding, Zhenhua published the artcileCobalt-Catalyzed Addition of Azoles to Alkynes, Quality Control of 72571-06-3, the publication is Organic Letters (2010), 12(18), 4180-4183, database is CAplus and MEDLINE.

A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.

Organic Letters published new progress about 72571-06-3. 72571-06-3 belongs to oxazolidine, auxiliary class Oxazole,Bromide,Benzene, name is 5-(4-Bromophenyl)oxazole, and the molecular formula is C9H6BrNO, Quality Control of 72571-06-3.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem