99488-35-4Relevant academic research and scientific papers
Reaction of chromone-3-carbaldehyde with α-amino acids-syntheses of 3- and 4-(2-hydroxybenzoyl)pyrroles
Figueiredo, Andrea G.P.R.,Tomé, Augusto C.,Silva, Artur M.S.,Cavaleiro, José A.S.
, p. 910 - 917 (2007)
Azomethine ylides generated from the reaction of chromone-3-carbaldehyde with α-amino acids undergo 1,5-electrocyclization reactions to afford 3- and 4-(2-hydroxybenzoyl)pyrroles. These ylides can be trapped with dipolarophiles in 1,3-dipolar cycloadditio
Integrating Metal-Catalyzed C-H and C-O Functionalization to Achieve Sterically Controlled Regioselectivity in Arene Acylation
Serratore, Nicholas A.,Anderson, Constance B.,Frost, Grant B.,Hoang, Truong-Giang,Underwood, Steven J.,Gemmel, Philipp M.,Hardy, Melissa A.,Douglas, Christopher J.
supporting information, p. 10025 - 10033 (2018/07/21)
One major goal of organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation is the most renowned method for the synthesis of aryl ketones, a common structural motif of many pharmaceuticals, agrochemicals, fragrances, dyes, and other commodity chemicals. However, an EAS synthetic strategy is only effective if the desired site for acylation is in accordance with the electronic-controlled regioselectivity of the reaction. Herein we report steric-controlled regioselective arene acylation with salicylate esters via iridium catalysis to access distinctly substituted benzophenones. Experimental and computational data indicate a unique reaction mechanism that integrates C-O activation and C-H activation with a single iridium catalyst without an exogenous oxidant or base. We disclose an extensive exploration of the synthetic scope of both the arene and the ester components, culminating in the concise synthesis of the potent anticancer agent hydroxyphenstatin.
Reactions of Formylchromone Derivatives. Part 5. Transformations of 3-Formylchromones into Pyrroles and Pyridines
Clarke, Paul D.,Fitton, Alan O.,Kosmirak, Mario,Suschitzky, Hans,Suschitzky, John L.
, p. 1747 - 1756 (2007/10/02)
4-Oxo-4H-1-benzopyran-3-carbaldehyde (3-formylchromone) (1) was treated with various bifunctional nucleophiles.With ethyl aminoethanoate it gave a mixture of ethyl 4-(2-hydroxybenzoyl)-6-(4-oxo-4H-1-benzopyran-3-yl)pyridine-2-carboxylate (2) and ethyl 4-(
