1267504-24-4Relevant academic research and scientific papers
First mechanosynthesis of piperlotines A, C, and derivatives through solvent-free Horner–Wadsworth–Emmons reaction
Ramírez-Marroquín, Oscar Abelardo,Manzano-Pérez, Flavio,López-Torres, Adolfo,Hernández-López, Alejandro,Cortés-Pacheco, Abimelek,Reyes-González, Miguel Angel
, p. 244 - 255 (2019)
Piperlotines are natural products characterized by an α,β-unsaturated amide moiety. These compounds found wide applications in Medicinal Chemistry like antibacterials, cytotoxic agents, anticoagulants, among others. To date, diverse methods of synthesis have been reported for piperlotines, but involving the use of catalysts, hazard reagents, anhydrous media or coupling reagents. Thus, in this work, we developed a greener method of synthesis of piperlotines A, C, and derivatives, through mechanochemical activation under solvent-free conditions. The reaction of a β-amidophosphonate, K2CO3, and an aromatic aldehyde afforded target compounds in moderate to good yields (46–77%), in an open atmosphere by grinding. It is worth to mention that this mechanochemical process was under thermodynamic control because just E isomer was isolated for every reaction. Moreover, synthesized piperlotines have been predicted by means of chemoinformatic analysis as potential therapeutic agents for the treatment of arthritis or cancer.
A general and selective iron-catalyzed aminocarbonylation of alkynes: Synthesis of acryl- and cinnamides
Driller, Katrin Marie,Prateeptongkum, Saisuree,Jackstell, Ralf,Beller, Matthias
supporting information; experimental part, p. 537 - 541 (2011/03/16)
Entering the iron age: The first general method for iron-catalyzed monocarbonylation of alkynes has been developed. A range of structurally diverse cinnamides and acrylamides have been obtained smoothly starting from commercially available amines and alkynes in the presence of [Fe 3(CO)12] and ligand L (see scheme). The method is highly chemo- and regioselective and requires no expensive catalyst.
