5510-44-1Relevant academic research and scientific papers
On the direct use of CO2 in multicomponent reactions: Introducing the Passerini four component reaction
Onwukamike, Kelechukwu Nnabuike,Grelier, Stéphane,Grau, Etienne,Cramail, Henri,Meier, Michael A. R.
, p. 31490 - 31495 (2018)
We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO2. Key to this approach is the use of a switchable solvent system, allowing the synthesis of a variety of α-carbonate-amides. The reaction was first investigated and optimized using butanol, isobutyraldehyde, tert-butyl isocyanide and CO2. Parameters investigated included the effect of reactant equivalents, reactant concentration, solvent, catalyst, catalyst concentration and CO2 pressure. Of the other parameters, the purity of the aldehyde and its tendency to oxidize was one of the most critical parameters for a successful P-4CR. After optimization, a total of twelve (12) P-4CR compounds were synthesized with conversions ranging between 16 and 82% and isolated yields between 18 and 43%. Their structures were confirmed via1H and 13C NMR, FT-IR and high resolution mass spectrometry (ESI-MS). In addition, three (3) hydrolysis products of P-4CR (α-hydroxyl-amides) were successfully isolated with yields between 23 and 63% and fully characterized (1H, 13C NMR, FT-IR and ESI-MS) as well.
Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture
Steuer, Christian,Gege, Christian,Fischl, Wolfgang,Heinonen, Karl H.,Bartenschlager, Ralf,Klein, Christian D.
supporting information; experimental part, p. 4067 - 4074 (2011/08/21)
The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds th
SmI2-mediated reduction of α-functionalised amides: Highly enantiospecific access to an atropisomeric amide
Hughes, Adam D.,Simpkins, Nigel S.
, p. 967 - 968 (2007/10/03)
SmI2 or SmI2-LiCl mixtures can be used to reduce α-functionalised amides in yields of up to 85% depending upon the amide structure. The method has been applied to the synthesis of an atropisomeric anilide system in highly enantioenriched form, starting with (S)-O-acetyl lactic acid.
