Synthesis of bis(glycosylamino)benzenes, derived from disaccharides lactose, maltose, and cellobiose, by direct condensation and their characterization are described.Glycosylamines belong to N glycosides and are of in terest for the food, textile, and rubber processing indus try. 1 Studies of properties of these carbohydrate deriva tives will help understanding of the fundamental aspects of carbohydrate chemistry. Hence, investigations into chemistry of glycosylamines are of importance for the development of both basic and applied aspects of science.To extend the array of N glycosides, we synthesized and characterized bisglycosylamine derivatives 1-9, in which o , m , or p phenylenediamine residues serve as the aglycones, and the disaccharides lactose (com pounds 1, 4, and 7), maltose (2, 5, and 8), and cellobiose (3, 6, and 9) represent the glycosidic moieties.Compounds 1-9 were synthesized by direct conden sation of diamines with carbohydrates in a molar ratio of 1 : 2. Taking into account poor solubilities of disaccha rides in alcohols that are often used as solvents in glycosylation of amines 2-4 and lower reactivities of disac charides in reactions with amines compared to monosac charides, 5 the reactions were carried out in the absence of a solvent with heating and distillation of water. The rate of formation of bis(glycosylamino)benzenes 1-9 depends on steric factors, in particular, on the mutual arrange ment of the amino groups in the phenylenediamine mol ecules. For example, bisglycosylation of o phenylenedi amine is completed in 6-8 h (depending on the di saccharide used), whereas the reactions with m and p phenylenediamines take, on the average, 3.5-4.5 h. Interestingly, glycosylation of o phenylenediamine with monosaccharides in an ethanolic medium, on the con trary, occurs more rapidly than the reactions with m and p phenylenediamines. This difference can be attributed to the fact that the formation of 1,2 bis(glycosylamino)ben zenes from monosaccharides occurs apparently via cyclic five membered aminal,** unlike glycosylation of m and p phenylenediamines, which occurs via Schiff bases. 1 Ap parently, the reactions of o phenylenediamine with dis accharides as the glycosylating agents proceed by a stan dard mechanism, i.e., via Schiff bases. 1 The composition and structures of the target products were confirmed by 13 C and 1 H NMR and IR spectro scopy. The 1 H NMR spectra of lactosylamines 1, 4, and 7
