30077-68-0Relevant academic research and scientific papers
Construction of 1,2,5-tricarbonyl compounds using methyl cyanoacetate as a glyoxylate anion synthon combined with copper(I) iodide-catalyzed aerobic oxidation
Kim, Se Hee,Kim, Ko Hoon,Kim, Jae Nyoung
supporting information; experimental part, p. 3335 - 3339 (2012/01/19)
A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β-position of α,β-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various α-aryl- and α-alkyl-α-keto esters have been synthesized using a similar approach. Copyright
Photochemical synthesis of highly functionalized cyclopropyl ketones
Wessig, Pablo,Muehling, Olaf
, p. 865 - 893 (2007/10/03)
A series of di- and trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3. The irradiation of 3 and 5 must be performed in the presence of an acid scavenger (1-methyl-1H-imidazole) to obtain the cyclopropanes 11 in good yields. The synthetic efficiency of the method was, among other things, demonstrated by the preparation of a highly strained bicyclo[2.1.0]pentane 11i in good yield. The mechanism of the photochemical cyclization was investigated by means of photokinetic measurements, as well as by quantum-chemical calculations. It was shown that the presence of the leaving group substantially influences all steps of the photochemical reaction cascade. The X-ray crystal structures of 11j and exo-11k were also determined.
Derives alkyles et aryles de l'acide nipecotique: synthese et appreciation de l'activite inhibitrice de la capture du GABA en fonction de parametres conformationnels et de biodisponibilite
Lapuyade, Gerard,Schlewer, Gilbert,N'Goka, Victor,Vernieres, Jean-Claude,Chambon, Jean-Pierre,et al.
, p. 383 - 392 (2007/10/02)
Alkyl and aryl derivatives of nipecotic acid: synthesis and inhibition of GABA uptake as a function of conformational parameters and bioavailability.Analogs of nipecotic acid, substituted at positions 2, 3, 4, 5, or 6 with a methyl or phenyl group were pr
