Heterocyclic Building Blocks-Oxazolidine

Takeuchi, Susumu published the artcileAsymmetric bis(alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper(I) triflate and a chiral bioxazoline ligand, Product Details of C14H24N2O2, the publication is Bulletin of the Chemical Society of Japan (2001), 74(5), 955-958, database is CAplus.

A palladium-catalyzed asym. bis(alkoxycarbonylation) reaction of terminal olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand, (4S,4’S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 °C to give the corresponding optically active mono-substituted succinates with enantioselectivity up to 66% ee.

Bulletin of the Chemical Society of Japan 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 C8H6ClN, Product Details of C14H24N2O2.

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

Onimura, Kenjiro published the artcileAsymmetric polymerization of N-substituted maleimides with organolithium-bisoxazolines complex, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Polymer Bulletin (Berlin) (1997), 39(4), 437-444, database is CAplus.

Asym. anionic polymerizations of achiral N-substituted maleimide (RMI) (N-cyclohexyl, N-Ph, and N-tert-Bu) by n-butyllithium (n-BuLi) or fluorenyllithium (FlLi) complexes of chiral bisoxazoline derivatives in toluene gave optically active polymers ([α]₄₃₅²⁵ -2.9 to -8.2°). The polymers prepared with initiator of n-BuLi-2,2′-bis(4,4′-isopropyl-1,3-oxazoline) showed neg. sp. rotations (poly(RMI), [α]₄₃₅²⁵ -5.8 to -8.2°) which were greater than those ([α]₄₃₅²⁵ -2.9 to -5.9°) with other chiral 2,2′-bis(4,4′-alkyl-1,3-oxazoline) (alkyl = iso-Bu and benzyl).

Polymer Bulletin (Berlin) 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, Application 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

Bredereck, Hellmut published the artcileFormamide reactions. I. Imidazole syntheses with formamide, SDS of cas: 20662-83-3, the publication is Chemische Berichte (1953), 88-96, database is CAplus.

α-HO, α-halo, α-NH₂, and, under reducing conditions, α-isonitroso ketones give 4,5-disubstituted imidazoles. Boiling 10 g. acetoin with 50 cc. HCONH₂ (I) 4 h. gives 55% 4,5-dimethylimidazole, HN.CH:N.CR:CR’ (II, R = R’ = Me) (III), b₁₁ 165-75°, m. 117° (HCl salt, m. 305°). Similarly, the following II (R = R’) are prepared (R, % yield, b.p., m.p., HCl salt (a) m.p. in the order given): Et, from propionoin, 67, b₁₀ 150-60°, 82-5°, a 252-3°; Pr, 81, b₁₀ 168°, 66°, a 163°; Bu, 72, b₁₁ 197-203°, -, a 147°; iso-Bu, 61, yellow oil, b. 177-9°, a (crystallizing with 1 H₂O) m. 72°, 131° (H₂O-free); Am, 51, light yellow oil, b₉ 210-16°, a 142°; C₆H₁₃, 45, -, -, a 130°; Me₂CH (IV), -, -, 214°, a 221° (formate salt, C₉H₁₆N₂.CH₂O₂ 85% yield, m. 140°; HBr salt, m. 225°). Refluxing 4 g. sebacoin with 15 cc. I 2 h. gives 87% 4,5-octamethyleneimidazole, needles, m. 229°, HCl salt m. 270°. 1-Cyclohexadecanol-2-one, b_0.03 156°, (8 g.) refluxed 2 h. with 50 cc. I gives 91% 4,5-tetradecamethyleneimidazole, leaflets, m. 115°, HCl salt m. 241°. 1,6-Diphenylpropionoin, b_0.05 180-90°, prepared in 53% yield from 29 g. PhCH₂CH₂CO₂Et and 8 g. Na in xylene, (5 g.) and 25 cc. I 2 h. give 66% II (R = R’ = PhCH₂CH₂), m. 112°. II are also prepared from benzoins, NH₂ ketones, and halogen ketones. Refluxing 10 g. benzoin with 20 cc. I 2 h. gives 91% II (R = R’ = Ph) (V), m. 231°; 10 g. furoin and 50 cc. I 2 h. give 89% II (R = R’ = α-furyl), m. 163°; p-dimethylaminobenzoin and I give 62% II [R = 4(5)-p-Me₂NC₆H₄, R’ = 5(4)-Ph], yellowish crystals, m. 230°; and 4 g. α-hydroxybutyrophenone and 20 cc. I 3 h. give 70% II (R = Ph, R’ = Et, or R and R’ may be interchanged), m. 172°. Refluxing 5 g. PhCOCHPhNH₂ 2 h. with 30 cc. I gives 90% V. Warming 10 g. benzilmonoxime with 70 cc. I and 3 cc. HCO₂H at 70° with slow addition of 2 g. NaHSO₃ and refluxing the mixture gently 1 h. give 71% V. Refluxing 8 g. PhCOCH₃Br and 50 cc. I 2 h. gives 90% II (R = Ph, R’ = H, or R and R’ may be interchanged), m. 128°; PhCOCHBrCHMe₂ and I give 69% II (R = Ph, R’ = Me₂CH, or R and R’ may be interchanged) b₁₅ 210-15°, m. 200°. PrCOCHBrEt and I 4 h. give 49% II (R = Et, R’ = Pr, or R and R’ may be interchanged), b₂₀ 185-95°; HCl salt m. 162°. Refluxing 25 g. MeCOCHBrMe and 100 cc. I 3 h. and fractionally distilling the product give 22% 4,5-dimethyloxazole, b₇₆₀ 129-35° [H₂PtCl₆ salt m. 240° (decomposition)], and 47% III, b₁₅ 170° (HBr salt, m. 265°). m-O₂NC₆H₄COCH₂Br and I 2 h. give 72% II (R = m-O₂NC₆H₄, R’ = H, or R and R’ may be interchanged), yellow crystals, m. 224°; p-MeO analog, 62%, leaflets, m. 137°.

Chemische Berichte 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, SDS of cas: 20662-83-3.

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

Adams, An published the artcileCharacterization of Model Melanoidins by the Thermal Degradation Profile, Computed Properties of 20662-83-3, the publication is Journal of Agricultural and Food Chemistry (2003), 51(15), 4338-4343, database is CAplus and MEDLINE.

Different types of model melanoidins (Maillard reaction products) were thermally degraded, with subsequent identification of the volatiles produced, to obtain and compare the thermal degradation profile of various melanoidins. At first, the volatiles produced from heated glucose/glycine standard melanoidins were compared with glucose/glutamic acid and L-(+)-ascorbic acid/glycine standard melanoidins. In the headspace of heated glucose/glycine melanoidins, mainly furans, were detected, accompanied by carbonyl compounds, pyrroles, pyrazines, pyridines, and some oxazoles. Heating of L-(+)-ascorbic acid/glycine melanoidins resulted in more N-heterocycles, while from glucose/glutamic acid melanoidins no N-heterocycles were formed. In a second part, a chem. treatment was applied to glucose/glycine melanoidins prior to the thermal degradation Acid hydrolysis was performed to cleave glycosidically linked sugar moieties from the melanoidin skeleton. Nonsol. glucose/glycine melanoidins were also subjected to an oxidation The results indicate that the thermal degradation profile is a useful tool in the characterization of different types of melanoidins.

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, Computed Properties of 20662-83-3.

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

Li, Bijin published the artcileUnexpected Sole Enol-Form Emission of 2-(2′-Hydroxyphenyl)oxazoles for Highly Efficient Deep-Blue-Emitting Organic Electroluminescent Devices, Product Details of C9H6BrNO, the publication is Advanced Functional Materials (2017), 27(9), n/a, database is CAplus.

Considerable efforts have been devoted to the development of highly efficient blue light-emitting materials. However, deep-blue fluorescence materials that can satisfy the Commission Internationale de l’Eclairage (CIE) coordinates of (0.14, 0.08) of the National Television System Committee (NTSC) standard blue and, moreover, possess a high external quantum efficiency (EQE) over 5%, remain scarce. Here, the unusual luminescence properties of triphenylamine-bearing 2-(2′-hydroxyphenyl)oxazoles (3a-3c) and their applications in organic light-emitting diodes (OLEDs) are reported as highly efficient deep-blue emitters. The 3a-based device exhibits a high spectral stability and an excellent color purity with a narrow full-width at half-maximum of 53 nm and the CIE coordinates of (0.15, 0.08), which is very close to the NTSC standard blue. The exciton use of the device closes to 100%, exceeding the theor. limit of 25% in conventional fluorescent OLEDs. Exptl. data and theor. calculations demonstrate that 3a possesses a highly hybridized local and charge-transfer excited state character. In OLEDs, 3a exhibits a maximum luminance of 9054 cd m^-2 and an EQE up to 7.1%, which is the first example of highly efficient blue OLEDs based on the sole enol-form emission of 2-(2′-hydroxyphenyl)azoles.

Advanced Functional Materials 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, Product Details of C9H6BrNO.

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

Aratani, Takahiro published the artcileAsymmetric bis(alkoxycarbonylation) reaction of cyclic olefins catalyzed by palladium in the presence of copper(I) triflate, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Bulletin of the Chemical Society of Japan (2012), 85(11), 1225-1232, database is CAplus.

A palladium-catalyzed asym. bis(alkoxycarbonylation) reaction of 1,2-dihydronaphthalene derivatives and related cyclic olefins in the presence of copper(I) triflate was achieved by using a chiral bis[oxazoline] ligand under normal pressure of carbon monoxide and oxygen to give the corresponding optically active cis-dicarboxylates with enantioselectivity up to 94% ee. An asym. intramol. and intermol. bis(alkoxycarbonylation) reaction of a prochiral diol possessing a dihydronaphthalene skeleton also proceeded enantioselectively by an appropriate selection of the substituent of a bis[oxazoline] ligand. The carbonylation product derived from 8-methoxy-1,2-dihydronaphthalene was applied to the synthesis of a biol. active hexahydrobenz[e]isoindole derivative Methoxycarbonylation of 1,2-dihydronaphthalene provided (1R,2R)-1,2,3,4-tetrahydro-1,2-naphthalenedicarboxylic acid di-Me ester (I). Thus, (1R,2R)-1,2,3,4-tetrahydro-5-methoxy-1,2-naphthalenedicarboxylic acid di-Me ester was elaborated into (3aR,9bR)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]isoindole (II). The synthesis of the target compounds was achieved using 1,2-dihydronaphthalene, 1H-indene, 6,7-dihydro-5H-benzocycloheptene as starting materials. The title compounds thus formed included (1R,2R)-2,3-dihydro-1H-indene-1,2-dicarboxylic acid di-Me ester and (5R,6R)-6,7,8,9-tetrahydro-5H-benzocycloheptene-5,6-dicarboxylic acid 5,6-di-Me ester, (2R,3R)-2-methyl-3-phenylbutanedioic acid 1,4-di-Me ester.

Bulletin of the Chemical Society of Japan 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

Vinay Kumar, Koravangala S. published the artcileA One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides, Name: 5-(4-Bromophenyl)oxazole, the publication is Synlett (2016), 27(9), 1363-1366, database is CAplus.

A new modified van Leusen strategy was developed for the synthesis of biol. significant 5-substituted oxazoles I (R = Ph, 2-furyl, etc.) by the reaction of either [(het)aryl]methyl alcs. RCH₂OH or benzyl bromides RCH₂Br as precursors with tosylmethyl isocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.

Synlett 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 C4H11NO, Name: 5-(4-Bromophenyl)oxazole.

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

Tran, Hai N. published the artcileNickel-Catalyzed Enantioselective Hydroboration of Vinylarenes, Computed Properties of 2185014-88-2, the publication is Organic Letters (2022), 24(1), 395-399, database is CAplus and MEDLINE.

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic Ni catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B₂pin₂) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me₄NF to activate B₂pin₂ is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Organic Letters 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 C2H4Cl2O3S, Computed Properties of 2185014-88-2.

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

Pullman, Bernard published the artcileElectronic aspects of the mechanism of thiamine-catalyzed reactions, SDS of cas: 20662-83-3, the publication is Biochimica et Biophysica Acta (1961), 576-87, database is CAplus and MEDLINE.

cf. CA 54, 22747e. The method of mol. orbitals was used to calculate the energy levels and the electronic distribution in thiamine and related model compounds The results were used to interpret the mechanism of thiamine-catalyzed reactions, and were consistent with the hypothesis that the active center of the coenzyme is the highly charged C₂ atom of its thiazolium ring. 35 references.

Biochimica et Biophysica Acta 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, SDS of cas: 20662-83-3.

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

Fan, Chunying published the artcileChemical compositions and copper(II) adsorption properties of sequentially extracted humic substances, including different humin fractions, Related Products of oxazolidine, the publication is Fresenius Environmental Bulletin (2018), 27(10), 6485-6499, database is CAplus.

Humin (HU) is the least understood humic substance (HS) fractions due to its close associations with soil mineral colloids. Here, humic acid (HA), fulvic acid (FA), HU, iron-bound HU (HUi), claybound HU (HUc) and residual HU (HUr) were sequentially extracted from an Alfisol of northeast China. Elemental anal., solid-state carbon-13 cross-polarization magic-angle-spinning NMR (13C CPMAS NMR) spectroscopy and pyrolysis-gas chromatog./mass spectrometry (Py-GC/MS) were used to characterize HS fractions. The adsorption isotherms of Cu(II) on HS fractions were obtained using batch equilibrium method. Among these HS fractions, HA contained higher proportion of phenols, whereas HUc exhibited higher proportion of aliphatic hydrocarbons. For the different HU fractions, n-alkanes/n-alkenes were particularly abundant in HUc, whereas polysaccharides were abundant in HUr. The adsorption of Cu(II) on HS fractions well fitted both Freundlich and Langmuir equations. The maximum amounts of Cu(II) adsorbed was FA > HUi > HA > HUc > HU > HUr, which was pos. correlated with their O/C ratio and carbonyl C whereas neg. correlated with C/N ratio (p < 0.01). The results suggested that HU is highly heterogeneous in terms of their chem. compositions and plays important role in controlling the behavior and fate of Cu(II) in the environment.

Fresenius Environmental Bulletin 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, Related Products of oxazolidine.

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