4122-54-7Relevant articles and documents
Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes
Kalkhambkar, Rajesh G.,Laali, Kenneth K.,Malunavar, Shruti S.,Prabhala, Pavankumar,Savanur, Hemantkumar M.,Sutar, Suraj M.
supporting information, (2020/04/08)
The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM][BF4] as solvent, and [PAIM][NTf2] as basic-IL, to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown.
Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling
Bonfio, Claudia,Caumes, Cécile,Duffy, Colm D.,Patel, Bhavesh H.,Percivalle, Claudia,Tsanakopoulou, Maria,Sutherland, John D.
supporting information, p. 3934 - 3939 (2019/03/08)
The main aim of origins of life research is to find a plausible sequence of transitions from prebiotic chemistry to nascent biology. In this context, understanding how and when phospholipid membranes appeared on early Earth is critical to elucidating the prebiotic pathways that led to the emergence of primitive cells. Here we show that exposing glycerol-2-phosphate to acylating agents leads to the formation of a library of acylglycerol-phosphates. Medium-chain acylglycerol-phosphates were found to self-assemble into vesicles stable across a wide range of conditions and capable of retaining mono- and oligonucleotides. Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.
Mild decarboxylative activation of malonic acid derivatives by 1,1′-carbonyldiimidazole
Lafrance, Danny,Bowles, Paul,Leeman, Kyle,Rafka, Robert
supporting information; experimental part, p. 2322 - 2325 (2011/06/26)
Chemical equations presented. Malonic acid derivatives undergo unusually mild decarboxylation when treated with N,N′-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield, which can be reacted further with a variety of nucleophiles in an efficient one-pot process.