1024019-25-7Relevant academic research and scientific papers
Functionalized β-lactams based on (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine and its imine–imine rearrangement initiated by potassium hydride
Valiullina,Selezneva,Khursan,Gimalova,Miftakhov
, p. 950 - 955 (2016)
Functionalized β-lactams were synthesized by reaction of (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)-methyl]methanimine with ketenes generated in situ from chloro- and dichloroacetic acids and 3-(methoxyimino) butanoic acid. (E)-1-(Furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine underwent imine–imine rearrangement by the action of potassium hydride to give thermodynamically more stable (E)-N-[(furan-2-yl)-methyl]-1-(4-methoxyphenyl)methanimine.
Intermolecular disproportionation between dimethyl (2-furylmethylidene)malonate and 4-methoxybenzylamine
Torosyan, Seda A.,Biglova, Yulia N.,Gimalova, Fanusa A.,Miftakhov, Mansur S.
, p. 429 - 430 (2016)
Sodium hydride-promoted disproportionation of the title compounds affords tetramethyl 2-(2-furyl)propane-1,1,3,3-tetracarboxylate and furfural N-(4-methoxybenzyl)imine.
Diastereo- A nd Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers
Green, Jacob C.,Zanghi, Joseph M.,Meek, Simon J.
supporting information, p. 1704 - 1709 (2020/02/20)
A Cu-catalyzed method for the efficient enantio- A nd diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable ?,?-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.
Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams
Cremonesi, Giuseppe,Croce, Piero Dalla,Fontana, Francesco,Rosa, Concetta La
, p. 554 - 561 (2008/09/20)
New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-β-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-β-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed.
