111600-87-4

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 536-74-3 phenylacetylene 
• 37067-95-1 2-iodo-1-methyl-1H-imidazole 

Relevant academic research and scientific papers

Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives

A variety of 2-alkynyl(benzo)imidazoles have been synthesized by dehydrogenative alkynylation of (benzo)imidazoles with terminal alkyne in NMP under air in the presence of Ag2CO3as the oxidant and Pd(OAc)2as the catalyst precursor. The data obtained in this study support a reaction mechanism involving a non-concerted metalation deprotonation (n-CMD) pathway.

Regiochemistry in cobalt-mediated intermolecular Pauson-Khand reactions of unsymmetrical internal heteroaromatic alkynes with norbornene

The intermolecular Pauson-Khand (PK) reactions of sterically comparable (2-phenylethynyl)heteroaromatic compounds with norbornene, mediated by Co 2(CO)8 to give cyclopentenone products, were examined in this study. A synthetic protocol utilizing focused-microwave dielectric heating proved indispensable in the efficient synthesis of the PK cyclopentenone products. "π-Deficient" heteroaromatic substrates, e.g., 2-pyrones, and some "π-excessive" heteroaromatics such as 2- and 3-thiophene and 2-furan favor the β-position in the newly formed cyclopentenone ring. Other π-excessive heteroaromatics such as 2-pyrrole or 2-indole favor the α-position. A π-excessive 3-indole derivative gave a nearly equal mixture of regioisomers. The position of the nitrogen in pyridyl-containing alkyne substrates also affects the regiochemical outcome of the PK reaction. A 2-pyridyl alkyne, possessing a proximal nitrogen, influences the regioselectivity relative to a 4-pyridyl variant quite dramatically, favoring the β-position in the newly formed cyclopentenone ring. A 2-pyrimidylalkyne exhibits similar behavior to the 2-pyridylalkyne. Compounds that do not participate in PK reactions with norbornene include (2-phenylethynyl)imidazoles and the related benzimidazoles, which promote rapid decomposition of the in situ generated (μ2-alkyne)Co2(CO)6 complexes. This stands in contrast with other nitrogen-containing heteroaromatics, e.g., pyrrole-, indole-, and pyrimidine-derived compounds, which effectively undergo PK reactions. Overall, the type of heteroaromatic group dramatically influences PK regioselectivity, which can in part be explained by rationalization of the current reaction mechanism, but not fully.

Phenylethynyl and styryl derivatives of imidazole and fused ring heterocycles

This invention relates to a compound and the use of the compound of the formula wherein R1, R2, R3, R4 and R5 are as defined in the description, A signifies —CH═CH— or —C≡C—; and B signifies wherein R

Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1,3-azoles

The palladium-catalyzed reactions of 4-bromo- and 5-bromothiazoles, as well as 4-bromo and 5-bromooxazoles with terminal acetylenes gave ethynyl derivatives in 43-89percent yields, whereas the reactions of 2-bromothiazoles and iodo-N-methylimidazoles affo