Glucose with aniline

Schiff, for example, had included carbohydrates in his studies on the formation of Schiff bases from aldehydes and amino compounds. He heated D-glucose with aniline or withp-toluidine in substantia [11], and described that these components, under loss of water, formed yellow glass-like condensation products. These supported his suggestions on the formation of Schiff bases from aldehydes and suitable aromatic amines [12]. 

Furfural is produced from glucose under the influence of acid and this reacts with aniline to yield a colored product [5]. 

Fig. 16 Cycloaddition reaction of 0-allyl derivative of D-glucose derives aldehyde with aniline...

Early evidence that the open-chain formula is, in itself, inadequate to explain the behavior of the glycosylamines emerged from the methylation experiments of Irvine and his coworkers." iV-Phenyl-D-glucosylamine was methylated to afford a crystalline tetramethyl ether which was hydrolyzed by acid to 2,3,4,6-tetra-O-methyl-D-glucose. Condensation of the latter compound with aniline afforded the original ether, which consequently must be 2,3,4,6-tetra-O-methyl-iV-phenyl-D-glucosylamine. 

Thebenol can be methylated to methebenol and acetylated on evaporation with 30 per cent, potassium hydroxide [7] or fusion with aniline hydrochloride [12] it is demethylated to northebenol, which, like thebenol itself, gives an iodhydrin on heating with concentrated hydriodic acid [7]. Thebenol contains an asymmetric carbon atom, but attempts to resolve it by condensing it with glucose residues yielded only decomposition products [12], The hydrocarbon pyrene [vi] is formed when thebenol is distilled with zinc-dust or reduced with hydriodic acid [7] pyrene is also obtained from thebaine under the same conditions [13]. 

Fig. 171. TLC of sugars on cellulose-MN layer using the solvent water-butanone-formic acid- er. butanol (15 + 30 + 15 4- 40) time of run 2 h visualisation with aniline phthalate 1 ribose 2 fucose 3 rhamnose 4 glucose 5 mannose 6 galactose ...

Encouraged by the enantioselectivity obtained with ketone 44a, a series of N-aryl-substituted ketones (examples shown in Scheme 3.12) were investigated to further understand the N-substituent effect on the epoxidation and to search for more practical ketone catalysts [24e,i]. Ketones such as 44b,c can be readily prepared in four steps in large quantities from inexpensive glucose and anilines [241],... 

Draw the a-N-glycoside and the p-N-glycoside formed when D-glucose is treated with aniline (C6H5NH2). 

Subsequently, Sorokin reported [14] the isolation of products with different properties from those of Schiff, when he reacted D-glucose and aniline at lower... 

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