One pot protecting group free synthesis of multifunctional biphenyl methyl-C-β-d-glycosides in aqueous medium

Recent developments in β-C-glycosides: synthesis and applications

“…Scheme 16. Synthesis of sugar-linked inden-1-ol derivatives.3.6 MCR reaction for biphenyl methyl-C-β β β β-D-glycosidesglycosides in aqueous medium 151. Multicomponent one-pot reaction of unprotected β-C-glycosidic ketones with aromaticaldehyde and malononitrile in the presence of K 2 CO 3 in aqueous medium leads to the formation of biphenyl methyl-C-β-D-glycosides.…”

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

“…61 Basic conditions of the Suzuki-Miyaura coupling using SiO 2 -supported Pd catalyst 62 could operate in the Knoevenagel condensation under aqueous conditions without the use of amine catalyst. 63 This situation allowed for a combination of the Suzuki-Miyaura coupling of aryl halides 61 and phenylboronic acid (62) A multicomponent reaction between aromatic aldehydes (64), 2-nitromethylenethiazolidine (65), and nitriles 66 in the presence of Et 3 N afforded a series of 5-amino-7-aryl-8-nitrothiazolo[3,2-a]pyridines (67) (Scheme 21, Table 4). 64 This one-pot multicomponent reaction was initiated by the Knoevenagel reaction of aldehyde with nitrile compound, followed by conjugated addition of enamine and cyclization.…”

“…65 The most probable mechanism as depicted in Figure 1 involves initially a Michael addition of malononitrile to the double bond of glycosyl butanone (68) resulting in an adduct (69). The latter, on the Knoevenagel condensation with another malononitrile in the presence of base B, gives an intermediate 70.…”

I2/K2CO3: An efficient catalyst for the synthesis of 5-aryl-2,6-dicyano-3-methylanilines

“…4 3,5-Diaryl-2,6-dicyanoanilines have been prepared from acetone and arylidenemalononitriles or 1-arylethylidenemalononitriles in the presence of piperidine. 5 The reaction between malononitrile and α,β-unsaturated ketones can also give 3,5-diaryl-2,6dicyanoanilines, but in poor yield (5-20%). 6 One-pot three-component reactions of aromatic aldehydes, mal- * For correspondence ononitrile and acetone in the presence of basic catalysts have also been reported to give the desired products.…”