1187772-35-5

Upstream product

• 273-53-0 benzoxazole 
• 33491-05-3 1-(2-bromoethynyl)-4-methylbenzene 
• 31638-66-1 (p-tolylethynyl)copper 
• 13673-62-6 2-methylsulfanyl-benzoxazole 
• 766-97-2 4-n-methylphenylacetylene 
• 104-87-0 4-methyl-benzaldehyde 
• 60512-56-3 1-(2,2-dibromovinyl)-4-methylbenzene 
• 4714-37-8 1-(2,2-dichlorovinyl)-4-methylbenzene 

Relevant academic research and scientific papers

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.

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.

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 direct C-H bond alkynylations of heteroarenes using gem-dichloroalkenes

Palladium-catalyzed direct alkynylations of heteroarenes were accomplished with inexpensive gem-dichloroalkenes as user-friendly electrophiles, which set the stage for a modular, step-economical synthesis of diversely decorated heteroaryl alkynes with amp

Nickel- and copper-catalyzed direct alkynylation of azoles and polyfluoroarenes with terminal alkynes under O2 or atmospheric conditions

The direct C-H alkynylation of azoles with terminal alkynes proceeds efficiently under a nickel/O2 catalytic system. On the other hand, a copper/air catalyst enables the coupling of polyfluoroarenes with terminal alkynes. These catalyses provide new accesses to arylacetylenes through the formal direct Sonogashira coupling.

Nickel-catalyzed direct alkynylation of azoles with alkynyl bromides

The direct C - H alkynylation of azoles with alkynyl bromides proceeds efficiently In the presence of a nickel-based catalyst system. The reaction enables the introduction of various alkynyl groups bearing aryl, alkenyl, alkyl, and silyl substituents to t