90548-40-6

Upstream product

• 273-53-0 benzoxazole 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 615-18-9 2-chloro-1,3-benzoxazole 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 13673-62-6 2-methylsulfanyl-benzoxazole 
• 100-52-7 benzaldehyde 
• 13146-23-1 copper(I) phenylacetylenide 
• 2579-22-8 Phenylpropargyl aldehyde 
• 95-55-6 2-amino-phenol 
• 7436-90-0 2,2-dibromostyrene 

Relevant academic research and scientific papers

One-pot sequential alkynylation and cycloaddition: Regioselective construction and biological evaluation of novel benzoxazole-triazole derivatives

Individually, benzoxazole and triazole moieties are of significant biological interest owing to their importance in drugs and pharmaceuticals. To assess their combined biological impact when woven into one molecule, we designed a novel, regioselective, multicomponent, one-pot (MCOP) approach for the construction of benzoxazole-linked triazoles. The synthesis has been achieved in two sequential steps involving copper-catalyzed alkynylation of benzoxazole followed by a 1,3-dipolar cycloaddition reaction. By combination of these two bioactive units into one core, a series of new benzoxazole-triazole scaffolds has been synthesized and subjected to in vitro antibacterial and anticancer evaluation. Tests against clinical isolates of Staphylococcus aureus and Escherichia coli showed potent Gram-negative activity for compounds 4{1,1,1}, 4{1,1,4}, and 4{1,2,1}. The cytotoxicity of the synthesized library was determined against three cancer cell lines: HeLa, SKBr3, and Hep G2. Compound 4{2,2,2} showed significant cytotoxicity against all the cell lines. These preliminary bioassay evaluations strongly suggest the promise and scope of these novel molecules as therapeutic agents in medical science.

Dehydrogenative and decarboxylative C-H alkynylation of heteroarenes catalyzed by Pd(II)-carbene complex

The direct alkynylation of heteroarenes was accomplished with easily prepared Pd(II) carbene complex (Pd Cat.) by two complementary strategies. Pd Cat. catalysed cross-dehydrogenative coupling of terminal alkynes with heteroarenes was achieved in the firs

Convenient synthesis of 2-alkynylbenzazoles through Sonogashira cross-coupling reaction between thioethers and terminal alkynes

We describe herein the synthesis of 2-alkynylbenzoxazole and 2-alkynylbenzothiazole derivatives through the Sonogashira cross-coupling reaction of the corresponding thioethers and terminal alkynes under aerobic conditions, using CuI and Pd(dppf)Cl2 as catalysts. The synthetic methodology allows the convenient cross-coupling of heteroaromatic substrates with a wide variety of aromatic and aliphatic alkynes, in moderate to good yields. The behavior of mercapto benzoxazoles and benzothiazoles were also investigated in the desulfitative Sonogashira cross-coupling reaction. It is noteworthy that the reaction occurred better under aerobic conditions rather than an inert atmosphere, although with increased amounts of the diyne side-product.

Novel preparation method of benzoxazole derivative

The present invention relates to a method for preparing an alkynylated bezoxazole derivative represented by chemical formula 1, and more specifically, to a method for preparing an alkynylated bezoxazole derivative by reacting a silver slat, propiolic acid, and benzoxazole compounds in the presence of a palladium catalyst and 1,3-bis(diphenylphosphino)propane as a phosphine-based catalyst.

Room-temperature direct alkynylation of arenes with copper acetylides

C-H bond in azoles and polyhalogenated arenes can be smoothly activated by copper acetylides to give the corresponding alkynylated (hetero)arenes by simple reaction at room temperature in the presence of phenanthroline and lithium tert-butoxide under an oxygen atmosphere. These stable, unreactive, and readily available polymers act as especially efficient and practical reagents for the introduction of an alkyne group to a wide number of arenes under remarkably mild conditions.

Palladium-catalyzed decarboxylative C-H alkynylation of benzoxazoles with α,β-ynoic acids

Palladium-catalyzed decarboxylative C-H alkynylation of benzoxazoles with α,β-ynoic acids was achieved for the first time. This straightforward method was found to be synthetically effective without strong base under air. Pd-catalyzed decarboxylative C-H alkynylation was developed through the reaction of benzoxazoles with a variety of -ynoic acids. This reaction proceeded smoothly via C-H functionalization in the presence of dppe and Ag2O without strong base under air. Copyright

Synthesis of internal alkynes through the Pd-catalyzed coupling of heteroaryl halides with terminal alkynes

Sonogashira-type cross-couplings of functionalized heterocyclic halides with terminal alkynes were performed efficiently at room temperature. The heteroaryl halides were easily prepared from the corresponding heterocyclic compounds. The catalytic system tolerated a very broad scope of substrates; oxazoles, thiazoles, and furans participate in this type of reaction for the first time. This reaction provides an efficient method for the direct functionalization of heterocycles. Sonogashira-type cross-coupling of functionalized heterocyclic halides with terminal alkynes are performed efficiently at room temperature. The catalytic system tolerates a very broad scope of substrates; oxazoles, thiazoles, and furans participate in this type of reaction for the first time. The reaction provides an efficient method for the direct functionalization of heterocycles. Copyright

Palladium-catalyzed C-H bond direct alkynylation of 5-membered heteroarenes: A well-defined synthetic route to azole derivatives containing two different alkynyl groups

A widely applicable oxidative coupling of 5-membered heteroarenes and terminal alkynes that uses a combination of palladium and silver salts was developed. Under suitable conditions, imidazole and benzimidazole, which are sluggish under similar previously reported oxidative coupling conditions, as well as imidazo[1,5-a]pyridines, oxazole, benzoxazole, thiazole, and benzothiazole could be alkynylated. In addition, the bromine atom on the substrates was intact under the reaction conditions, and conventional Sonogashira coupling did not occur at all. With these reactivities in hand, a well-defined synthetic route to imidazo[1,5-a]pyridines and thiazole containing two different alkynyl groups was achieved in a simple manner. In addition, linear correlations were observed between the fluorescence wavelength and the Hammett substituent constants of aryl groups, not only on the C1- but also on the C3-alkynyl group of the obtained 1,3-bis(arylethynyl)imidazo [1,5-a]pyridines.

Palladium-catalyzed oxidative alkynylation of heterocycles with terminal alkynes under air conditions

Pd-Catalyzed oxidative alkynylation of azoles with terminal alkynes was developed via simultaneous activation of both heterocyclic sp2 C-H and alkynyl sp C-H bonds. The choice of palladium catalyst source and external base resulted in being imp

Facile preparation of 2-substituted benzoxazoles and benzothiazoles via aerobic oxidation of phenolic and thiophenolic imines catalyzed by polymer-incarcerated platinum nanoclusters

Platinum nanoclusters supported on a polymer/carbon black composite material was found to be an excellent catalyst for the oxidative cyclization of phenolic and thiophenolic Schiff bases to 2-substituted benzoxazoles and benzothiazoles under ambient conditions. Copyright