Category: benzoxazole

Ishekuts, B.’s team published research in Farmakologiya i Toksikologiya (Moscow) in 1961 | CAS: 5233-42-1

Diuretic effects of dihydrochlorothiazide derivatives. Recommended basis is hydrochlorothiazide 20. Products is: https://www.ambeed.com/products/742-20-1.html, 432499-63-3

1. The impurity of diuretic hydrochlorothiazide 04, also be a medical intermediate.
2. It’s mainly used for the detection of drug impurities, the synthesis of hydrochlorothiazide and the screening of medical structural fragments.
3. Presents a weak alkaline,refrigeration.

. Recommended Products is: 5250-72-6 and 22503-72-6.

Chlorothiazide, 6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,l-dioxide, yields a 3,4-dihydro derivative, hypothiazide (I). Taking the diuretic and saluretic activities (in rats) of chlorothiazide as 1, resp. activities of I were 4.1, 10.8; among derivatives, peak activity (16.0, 40.0) was reached with pentamethylene instead of the 2 H atoms in the 3-position. Other activating substitutions were 5-Cl (5.8, 4.0); 3-Me (1.7, 4.0); 3-CCl3 (1.1, 6.2); and ring rupture at 2 to form 1-SO2NH2 and NHCH2OMe groups (3.5, 7.5). Other substitutions, giving activities less than 1, were 6-NH2, 3-H (no activity), 5-Br. After ring rupture the groups SO2NHMe (0.7, 0.9) and SO2NEt2 (0,0) lowered activity. Effective diuretic doses (mg./kg.) were determined for I derivatives in which the 3-CH2 group is replaced: CHEt 0.5; CHCH:CH2 0.2; CHCH:CHMe 1.0; and side rings, 4-methylcyclohexyl 4.0; cyclopentyl 0.2; thiacyclohexyl 0.2; dithiacyclopentyl 0.1; piperidyl 4.0; N-ethylpiperidyl 4.0; I 0.2. The relatively inactive N-ethylpiperidyl derivative had a pronounced hypotensive effect.

Diuretic effects of dihydrochlorothiazide derivatives. Recommended basis is hydrochlorothiazide 20. Products is: https://www.ambeed.com/products/742-20-1.html, 432499-63-3

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Chen, Zhiyuan’s team published research in Journal of Organic Chemistry in 2016-10-07 | CAS: 50578-18-2

Transition-Metal-Catalyzed Hydrosulfoximination and Oxidation Reaction for the Synthesis of Sulfoximine Derivatives. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

1-Iminotetrahydrothiophene 1-oxide (BD00963737) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 83730-53-4.

We report herein a Au/Ag-cocatalyzed chemoselective hydrosulfoximination reaction of simple ynamides with free NH-sulfoximines, which produces the N-alkenylated sulfoximidoyl derivatives with quant. atom efficiency and good to excellent yields. Further elaborations of the enamine isomers under Ru-catalyzed oxidative conditions to cleave the C:C double bonds can selectively afford urea-type sulfoximines. The aforementioned catalytic reactions provide new opportunities for the convergent and straightforward access to sulfoximine derivatives

Transition-Metal-Catalyzed Hydrosulfoximination and Oxidation Reaction for the Synthesis of Sulfoximine Derivatives. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cobo, Angel A.’s team published research in Organic Letters in 21 | CAS: 1239015-11-2

Organic Letters published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C33H29N3O3, Recommanded Product: (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole).

Cobo, Angel A. published the artcileCatalytic Asymmetric Synthesis of Cyclopentene-spirooxindoles Bearing Vinylsilanes Capable of Further Transformations, Recommanded Product: (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), the publication is Organic Letters (2019), 21(20), 8196-8200, database is CAplus and MEDLINE.

The authors report a Sc-catalyzed [3 + 2] annulation of alkylideneoxindoles with allenylsilanes for the enantioselective formation of cyclopentene-spirooxindoles containing vinylsilanes. Using a Sc(OTf)2/PyBOX/BArF complex, the spiroannulation of allenylsilanes affords products with >94:6 dr and >90:10 er. The effect of the counterion and ligand to control selectivity is discussed. The transformation of the vinylsilane is demonstrated using cross-coupling, epoxidation, and Tamao-Fleming oxidation reactions. Competition experiments provide a comparison of nucleophilicity between allyl- and allenylsilanes.

Organic Letters published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C33H29N3O3, Recommanded Product: (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole).

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Ratni, Hasane’s team published research in Journal of Medicinal Chemistry in 59 | CAS: 866332-15-2

Journal of Medicinal Chemistry published new progress about 866332-15-2. 866332-15-2 belongs to benzoxazole, auxiliary class Boronic acid and ester,Benzooxazole,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (2-Methylbenzo[d]oxazol-6-yl)boronic acid, and the molecular formula is C8H8BNO3, Related Products of benzoxazole.

Ratni, Hasane published the artcileSpecific Correction of Alternative Survival Motor Neuron 2 Splicing by Small Molecules: Discovery of a Potential Novel Medicine To Treat Spinal Muscular Atrophy, Related Products of benzoxazole, the publication is Journal of Medicinal Chemistry (2016), 59(13), 6086-6100, database is CAplus and MEDLINE.

Spinal muscular atrophy (SMA) is the leading genetic cause of infant and toddler mortality, and there is currently no approved therapy available. SMA is caused by mutation or deletion of the survival motor neuron 1 (SMN1) gene. These mutations or deletions result in low levels of functional SMN protein. SMN2, a paralogous gene to SMN1, undergoes alternative splicing and exclusion of exon 7, producing an unstable, truncated SMNΔ7 protein. Herein, we report the identification of a pyridopyrimidinone series of small mols. that modify the alternative splicing of SMN2, increasing the production of full-length SMN2 mRNA. Upon oral administration of our small mols., the levels of full-length SMN protein were restored in two mouse models of SMA. In-depth lead optimization in the pyridopyrimidinone series culminated in the selection of compound 3 (RG7800) (I), the first small mol. SMN2 splicing modifier to enter human clin. trials.

Journal of Medicinal Chemistry published new progress about 866332-15-2. 866332-15-2 belongs to benzoxazole, auxiliary class Boronic acid and ester,Benzooxazole,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (2-Methylbenzo[d]oxazol-6-yl)boronic acid, and the molecular formula is C8H8BNO3, Related Products of benzoxazole.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Zhou, You-Yun’s team published research in Angewandte Chemie, International Edition in 52 | CAS: 1239015-11-2

Angewandte Chemie, International Edition published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C27H39ClN2, Related Products of benzoxazole.

Zhou, You-Yun published the artcileHighly Enantioselective [3+3] Cycloaddition of Aromatic Azomethine Imines with Cyclopropanes Directed by π-π Stacking Interactions, Related Products of benzoxazole, the publication is Angewandte Chemie, International Edition (2013), 52(5), 1452-1456, database is CAplus and MEDLINE.

A new role of the ligands with sidearm group in a nickel catalyzed [3+3] cycloaddition reaction of isoquinoline azomethineimines with cyclopropanes, in which a prominent π-π stack-directing effect of the sidearm proved to be crucial to the stereochem. control.

Angewandte Chemie, International Edition published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C27H39ClN2, Related Products of benzoxazole.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Chen, Jiang-Hua’s team published research in Tetrahedron in 68 | CAS: 1239015-11-2

Tetrahedron published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C33H29N3O3, Application of (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole).

Chen, Jiang-Hua published the artcileTris(oxazoline)/copper-catalyzed coupling of alkynes with nitrones: a highly enantioselective access to β-lactams, Application of (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), the publication is Tetrahedron (2012), 68(25), 5042-5045, database is CAplus.

Chiral tris(oxazoline)/Cu(I) complexes are demonstrated as a type of efficient catalysts for the asym. Kinugasa reaction of terminal alkynes with C-arylnitrones, providing a highly enantio- and diastereoselective access to optically active β-lactams. For example, reacting PhCCH with PhN+(O–):CHPh in the presence of CuOTf and tris(oxazoline) I gave β-lactam II as the major isomer.

Tetrahedron published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C33H29N3O3, Application of (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole).

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Dong, Zhe’s team published research in Nature (London, United Kingdom) in 598 | CAS: 1207294-92-5

Nature (London, United Kingdom) published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Computed Properties of 1207294-92-5.

Dong, Zhe published the artcileMetallaphotoredox-enabled deoxygenative arylation of alcohols, Computed Properties of 1207294-92-5, the publication is Nature (London, United Kingdom) (2021), 598(7881), 451-456, database is CAplus and MEDLINE.

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis.

Nature (London, United Kingdom) published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Computed Properties of 1207294-92-5.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Sakai, Holt A.’s team published research in Journal of the American Chemical Society in 144 | CAS: 1207294-92-5

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application In Synthesis of 1207294-92-5.

Sakai, Holt A. published the artcileNontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)-C(sp3) Cross-Coupling via Radical Sorting, Application In Synthesis of 1207294-92-5, the publication is Journal of the American Chemical Society (2022), 144(14), 6185-6192, database is CAplus and MEDLINE.

In this report, the C(sp3)-C(sp3) cross-coupling of alcs. and carboxylic acids through the dual combination of N-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation were described. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcs. or tertiary carboxylic acids. Synthetic applications of this methodol. to alc. C1-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomols. were demonstrated.

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application In Synthesis of 1207294-92-5.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Wright, Adam J.’s team published research in European Journal of Inorganic Chemistry in 2022 | CAS: 1239015-11-2

European Journal of Inorganic Chemistry published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C6H10O7, Formula: C33H29N3O3.

Wright, Adam J. published the artcilePlanar Chiral Pseudo-Isocoumarins by Copper Catalysed Desymmetrisation, Formula: C33H29N3O3, the publication is European Journal of Inorganic Chemistry (2022), 2022(12), e202100841, database is CAplus.

A new Cu catalyzed desymmetrization reaction of bisalkynyl ferrocenecarboxylic acids using (R,R)-Ph-Pybox results in the 1st asym. synthesis of planar chiral pseudo-isocoumarins in up to 64% enantiomeric excess and up to 99% yield with complete regioselectivity. Tri-functionalized planar chiral ferrocenes were synthesized in five steps from com. available materials, without the need for traditional directing group chem. via an easily diversified route exploiting the double Sonogashira coupling reaction. The absolute configuration of the chiral heterocycles is proven by chem. correlation and CD spectroscopy giving the asym. reaction synthetic utility and opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives

European Journal of Inorganic Chemistry published new progress about 1239015-11-2. 1239015-11-2 belongs to benzoxazole, auxiliary class TOX Ligands, name is (3aS,3a’S,3a”S,8aR,8a’R,8a”R)-2,2′,2″-(Propane-1,2,2-triyl)tris(8,8a-dihydro-3aH-indeno[1,2-d]oxazole), and the molecular formula is C6H10O7, Formula: C33H29N3O3.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Intermaggio, Nicholas E.’s team published research in Journal of the American Chemical Society in 144 | CAS: 1207294-92-5

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application of 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate.

Intermaggio, Nicholas E. published the artcileDeoxytrifluoromethylation of Alcohols, Application of 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, the publication is Journal of the American Chemical Society (2022), 144(27), 11961-11968, database is CAplus and MEDLINE.

Deoxy-functionalization of alcs. represents a class of reactions that has had profound impact on modern medicine. In particular, deoxyfluorination is commonly employed as a means to incorporate high-value fluorine atoms into drug-like mols. Recently, the trifluoromethyl (CF3) group has garnered attention from medicinal chemists due to its ability to markedly improve the pharmaceutical properties of small mol. drug candidates. To date, however, there remains no general means to accomplish the analogous deoxygenative trifluoromethylation of alcs. Herein, a copper metallaphotoredox-mediated direct deoxytrifluoromethylation is reported, wherein alc. substrates are activated in situ by benzoxazolium salts for C(sp3)-CF3 bond formation.

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application of 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem