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Cyanoguanidine as a versatile, eco-friendly and inexpensive reagent for the synthesis of 2-aminobenzoxazoles and 2-guanidinobenzoxazoles

An effective, easy-to-handle, safe and inexpensive protocol is reported for the synthesis of 2-aminobenzoxazoles under Lewis acid activation, utilising cyanoguanidine as the cyanating reagent. An optimized procedure for the synthesis of 2-guanidinobenzoxazole and novel derivatives is also described.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Alkylation of Aromatic Amines with Trialkyl Amines Catalyzed by a Defined Iridium Complex with a 2-Hydroxypyridylmethylene Fragment

Six Cp?Ir complexes containing NN-bitentate chelate ligands [Cp?IrCl(C5H4CH2C5H3OH)][Cl] (1), [Cp?IrCl(C5H4CH2C5H3O)] (2), [Cp?IrCl(C5H4C5H3OH)] [Cl] (3), [Cp?IrCl(C5H4CH2C5H4)][Cl] (4), [Cp?IrCl(CH3OC5H3CH2C5H3OCH3)][Cl] (5), and [Cp?IrCl(CH3OC5H3CH2C5H3OH)][Cl] (6) were synthesized and characterized. Complex 1 could be transformed to 2 when reacted with NaOtBu or NEt3 via -OH deprotonation. These six complexes were tested as catalysts for mono-N-alkylation of amines with trialkyl amines, and complex 1 exhibited highest activity. The coupling reactions proceed under air condition, with 1 mol % catalyst loading without extra base in methanol at 120 C and can be further accelerated by adding NR3¡¤HCl.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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COMBINATIONS COMPRISING HISTONE DEACETYLASE INHIBITORS

The invention relates to a combination of a compound of formula (I) or a pharmaceutically acceptable salt thereof, and at least one second agent selected from the group consisting of proteasome inhibitors, tumour immunotherapeutics or immunomodulatory agents, signal transduction pathway inhibitors, agents inhibiting the BCL2 family of proteins, agents inhibiting Mcl-1, poly (ADP-ribose) polymerase (PARP) Inhibitors, aromatase inhibitors, conventional cytotoxic agents or a miscellaneous agent selected from abiraterone, ARN-509 and MYC inhibitors.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Bunte Salt CH2FSSO3Na: An Efficient and Odorless Reagent for Monofluoromethylthiolation

A practical and efficient monofluoromethylthiolation that employs the typical Bunte salt, sodium S-(fluoromethyl) sulfurothioate, as the sulfur source is described. This reagent reacts readily with a variety of aryl amines and aryl thiols. The high tolerance of functional groups demonstrates the potential of this reaction. In addition, this method is suitable for the late-stage monofluoromethylthiolation of complex bioactive molecules.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Radical C-H functionalization to construct heterocyclic compounds

Heterocyclic compounds are widely present in natural products, pharmaceuticals and bioactive molecules. Thus, organic and pharmaceutical chemists have been making extensive efforts to construct those heterocyclic frameworks through developing versatile and efficient synthetic strategies. The direct C-H functionalization via the radical pathway has emerged as a promising and dramatic approach towards heterocycles with high atom- and step-economy. Heterocyclic compounds such as coumarins, furans, benzofurans, xanthones, benzothiazoles, indoles, indolines, oxindoles, quinolines, isoquinolines, quinoxaline, and phenanthridines have been successfully synthesized by C-H functionalization through the radical pathway. In this review, recent advances on radical C-H functionalization to construct heterocyclic compounds are highlighted with discussions.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Phosphine-Free Well-Defined Mn(I) Complex-Catalyzed Synthesis of Amine, Imine, and 2,3-Dihydro-1 H-perimidine via Hydrogen Autotransfer or Acceptorless Dehydrogenative Coupling of Amine and Alcohol

The application of nontoxic, earth-abundant transition metals in place of costly noble metals is a paramount goal in catalysis and is especially interesting if the air- and moisture-stable ligand scaffold is used. Herein, we report the synthesis of amines/imines directly from alcohol and amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines and amines can be obtained from the same set of alcohols and amines using the same catalyst, only by tuning the reaction conditions. The amount and nature of the base are found to be a highly important aspect for the observed selectivity. Both the primary and secondary amines have been employed as substrates for the N-alkylation reaction. As a highlight, we showed the chemoselective synthesis of resveratrol derivatives. Furthermore, the Mn-catalyzed dehydrogenative synthesis of structurally important 2,3-dihydro-1H-perimidines has also been demonstrated. Density functional theory calculations were also carried out to model the reaction path and to calculate the reaction profile.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Inter- and intramolecular Diels-Alder reaction of benzoxazole-based azadienes

Inter- and intramolecular Diels-Alder reactions of novel azadienes 2 and 3 are described. The dienes 2 and 3 react with electron-rich dienophiles, vinyl ethers 7a,b and p-methoxystyrene derivatives 7c,d to afford the corresponding cycloadducts 8 and 9, regioselectively. The azadienes 2 and 3 also undergo tandem transesterification and intra-molecular cycloaddition with cinnamyl alcohols 13 in the presence of stannoxane catalyst 14 to give tetracyclic compounds 15 and 16 in one step. In a tandem process, the geometries of the dienophile components of 13 were transmitted into the cycloadducts 15 and 16.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells

Acid ceramidase (AC) hydrolyzes ceramides, which are central lipid messengers for metabolism and signaling of sphingolipids. A growing body of evidence links deregulation of sphingolipids to several diseases, including cancer. Indeed, AC expression is abnormally high in melanoma cells. AC inhibition may thus be key to treating malignant melanoma. Here, we have used a systematic scaffold exploration to design a general pharmacophore for AC inhibition. This pharmacophore comprises a 6 + 5 fused ring heterocycle linked to an aliphatic substituent via a urea moiety. We have thus identified the novel benzimidazole derivatives 10, 21, 27, and 30, which are highly potent AC inhibitors. Their chemical and metabolic stabilities are comparable or superior to those of previously reported AC inhibitors. Moreover, they are potent against endogenous AC in intact melanoma cells. These novel inhibitors merit further characterization and can serve as a promising starting point for the discovery of new antimelanoma therapeutics.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Synthesis of amide-linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials

Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds (7-9) were prepared from N-benzazolylcarbamoylmethylcinnamamides (1-3) adopting eco-friendly synthetic methodologies. In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1-3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz, IR, NMR, and mass spectra and were assayed for antimicrobial activity. Among all the tested compounds, 8a and 8c displayed excellent antibacterial activity, whereas 9a and 9c showed promising antifungal activity.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem