14489-84-0Relevant academic research and scientific papers
Rapid and efficient access to secondary arylmethylamines
Fleury-Brégeot, Nicolas,Raushel, Jessica,Sandrock, Deidre L.,Dreher, Spencer D.,Molander, Gary A.
supporting information; experimental part, p. 9564 - 9570 (2012/08/28)
Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes. Secondary ammoniomethyltrifluoroborates can be easily synthesized by nucleophilic substitution on potassium bromomethyltrifluoroborate. These reagents have then been used in Suzuki-Miyaura cross-couplings with aryl bromides, offering an effective access to the aminomethylarene structural motif. This new method provides an interesting alternative to the reductive amination procedure (see scheme). Copyright
Cycloadditions, XX, Thermally Induced Intramolecular Reactions of 2-Methyl-2,3-butadienamides
Himbert,Gerhard,Schlindwein, Hans-Juergen
, p. 1785 - 1794 (2007/10/02)
The 2-methyl-2,3-butadienamides 4a-m are directly synthesized by the reaction of the corresponding allenic acid chloride 2 with the secondary amines 3.At heating, 4a-j undergo the intramolecular Diels-Alder reaction, by using their ω-standing double bond and the ?-system of the directly bonded phenyl groups or of the "methylenic" bonded arenes of furans.Thereby the tricycles 6a-g (bearing five-membered lactam moieties) and/or the tricycles 7-9 (bearing six-membered lactam moieties) are formed.The influence of the geminal methyl group on the chemoselectivity and on the velocity of the IMDA reactions is investigated.The N-allyl derivatives of 4 (s. 4l and m) form the bicycles 10 by intramolecular -Cycloaddition. Key words: 2-Methyl-2,3-butadienamides, Intramolecular - and -Cycloadditions
Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics
Stuetz, Anton,Georgopoulos, Apostolos,Granitzer, Waltraud,Petranyi, Gabor,Berney, Daniel
, p. 112 - 125 (2007/10/02)
Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.
