The diastereospecific formation of β-N-glycoside-linked α-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl(2)·Et(2)O as a promoter in Et(2)O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl α-amino-2(5H)-furanone 5, ...

The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized alpha- and beta-am...

is a bis-Mannich base. Mannich bases have various biological activities such as antimicrobial, cytotoxic, anticancer, analgesic, and anticonvulsant activities. It has been reported that Mannich bases such as 1-diphenylaminomethyl-3-(1-naphthylimino)-1,3-dihydroindol-3-one, 1diphenylaminomethyl-3-(4-methylphenylimino)-1,3-dihydroindol-3-one and 1,3-dicyclohexyl-5-alkyl-5-aminomethylbarbituric ac...

A ttem pted M annich reaction with the title com pound 1 using m orpholine and formalin led to 2 or 4 according to the reaction conditions. W hereas, on using prim ary amines the diindeno [l,2-b:2 ',l'-e]pyridine (9 -1 1 ) were obtained, in addition to 2-methylene1,3-indandione (6 ), in case o f 10 and 11. However, the M annich bases 1 3 -1 5 were form ed on treating 2-benzylidene-1,3-indandion...

The Mannich base containing ciprofloxacin and kojic acid structural units was prepared and evaluated in antitumor activity. The enhancement in antitumor activity was observed both from the Mannich base (IC(50): 103.3±5.0 µM for HepG2, 87.9±8.0 µM for HCT-116 cell) and its copper complex (IC(50): 11.5±1.8 µM for HepG2, 44.4±2.5 µM for HCT-116 cell) compared to the ciprofloxacin and kojic acid. T...

Abstract A highly diastereo‐ and enantioselective Mannich reaction of α ‐acetoxy‐ β ‐keto esters with isatin imine was developed. The quinine thiourea organocatalyst smoothly promoted the asymmetric to furnish various 3‐substituted‐3‐aminooxindole derivatives bearing two adjacent tetra‐substituted stereocenters in up 93 % yield, 98 ee >20 : 1 dr . transition state structure absolute configur...

A copper-catalyzed synthesis of 2-(aminomethyl)indole through domino three-component coupling-cyclization has been developed. This reaction proceeds through Mannich-type coupling of 2-ethynylanilines, aldehydes, and secondary amines, followed by hydroamination. This indole formation was applicable to the synthesis of 4-methylene-2,3,4,9-tetrahyro-1H-pyrido[3,4-b]indoles and 5,6,7,8-tetrahydrobe...

An efficient metal-free visible light-driven two-step domino reaction towards new bioactive tetrahydroisoquinoline-butenolide hybrid compounds was developed for the first time. Combination of fluorescein as photosensitizer and thiourea an additive found to be most effective way promote aerobic amine oxidation/vinylogous Mannich sequence with yields up 97% a broad substrate scope. Both experimen...