10345-67-2Relevant academic research and scientific papers
Anionic, in situ generation of formaldehyde: A very useful and versatile tool in synthesis
Deguest, Geoffrey,Bischoff, Laurent,Fruit, Corinne,Marsais, Francis
, p. 1165 - 1167 (2007)
(Chemical Equation Presented) A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.
Synthesis and Structure-Activity Relationships of Triazaspirodecanone Derivatives as Nociceptin/Orphanin FQ Receptor Ligands
Corrado, Sandra,Battisti, Umberto M.,Sorbi, Claudia,Tait, Annalisa,Malfacini, Davide,Camarda, Valeria,Calò, Girolamo,Brasili, Livio
, p. 447 - 458 (2015)
Several spiroxatrine derivatives were synthesized and evaluated as potential NOP receptor ligands. Structural modifications of the 1,4-benzodioxane moiety of spiroxatrine have been the focus of this research project. The structure-activity relationships that emerged indicate that the presence of an H-bond donor group (hydroxyl group) is more favorable for NOP activity when it is positioned α with respect to the CH2 linked to the 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one portion. Moreover, cis diastereoisomers of the hydroxyl derivatives4 and 22 show a moderately higher degree of stereoselectivity than trans isomers. In particular, the spiropiperidine derivative cis-4 has submicromolar agonistic activity, and it will be the reference compound for the design and synthesis of new NOP agonists.
Lewis base catalysis by thiourea: N -bromosuccinimide-mediated oxidation of alcohols
Tripathi, Chandra Bhushan,Mukherjee, Santanu
experimental part, p. 1592 - 1598 (2012/03/11)
In recent times, (thio)urea derivatives have become synonymous with hydrogen bonding owing to their extensive applicability as small molecule organocatalysts. In this paper, another activation mode by thiourea derivatives, namely via Lewis base catalysis, is disclosed for the NBS-mediated oxidation of alcohols. The mild reaction conditions employed here is suitable for chemoselective oxidation of secondary alcohol in the presence of primary alcohol.
Proline-catalyzed facile access to Mannich adducts using unsubstituted azoles
Srinivas, Nagarapu,Bhandari, Kalpana
body text, p. 7070 - 7073 (2009/04/07)
A novel and facile method for the direct construction of C-C-N bond with unsubstituted azoles under Mannich conditions is developed for the first time. The reaction is catalyzed efficiently by l-proline to give the Mannich adducts 1a-10b in DMSO, whereas in water, insertion of two successive bonds, C-C-N and C-C-O occurred to give compounds 11a-20b. The latter are deformylated readily into the desired products 1a-10b under basic conditions. Mechanistic aspects for the formation of these products are discussed.
Expeditious and Efficient Annulation Protocol for the Synthesis of α,β-Unsaturated δ-Lactones from β-Keto Esters
Nangia, A.,Rao, P. Bheema
, p. 2375 - 2378 (2007/10/02)
β-Keto esters 6a-e are transformed into β-keto alcohols 7a-e, which are homologated to phosphonates 9a-e.Intramolecular Horner-Wadsworth-Emmons reaction affords δ-lactones 10a-d in excellent overall yields. Key words: δ-Lactones; β-Keto esters; Intramolecular; Phosphonates; Horner-Wadsworth-Emmons
