Chemistry of Non-Enzymic Browning. VI. The reaction of Aldoses with Amine Bisulphites

1959 ◽  
Vol 12 (2) ◽  
pp. 275 ◽  
Author(s):  
DL Ingles
Keyword(s):  
Cation Exchange ◽  
Exchange Resin ◽  
Cation Exchange Resin ◽  
Addition Compound ◽  
Enzymic Browning ◽  
New Compounds

The crystalline glucose-aniline bisulphite addition compound, D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl anilinium sulphonate, was prepared from the reaction of D-glucose with aniline bisulphite in water and in methanol. The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl piperidinium sulphonate was prepared by adding piperidine bisulphite to preformed N-phenyl-D-glucosylamine. Other new compounds of similar structure were prepared from the reaction of aniline bisulphite with D -galactose and D-mannose. cycloHexylamine bisulphite reacted with D-glucose to form crystalline D-glycero-D-ido-1,2,3,4,5,6-hexahydroxyhexyl cyclohexylammonium sulphonate. When treated with aniline this compound formed D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl cyclohexylammonium sulphonate. The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl potassium and anilinium sulphonates were interconverted by use of a cation-exchange resin. Acetylation of the anilinium sulphonate in pyridine gave the tetra-acetate of N-phenyl-D-glucosylamine.

Synthesis of 3,4-Dihydropyrano[c]chromenes Using Carbon Microsphere Supported Copper Nanoparticles (Cu-NP/C) Prepared from Loaded Cation Exchange Resin as a Catalyst

2019 ◽  
Vol 16 (2) ◽  
pp. 288-293
Author(s):  
Yogesh W. More ◽  
Sunil U. Tekale ◽  
Nitishkumar S. Kaminwar ◽  
László Kótai ◽  
Tibor Pasinszki ◽  
...  
Keyword(s):  
Raman Spectroscopy ◽  
Cation Exchange ◽  
Copper Nanoparticles ◽  
Exchange Resin ◽  
Cation Exchange Resin ◽  
Environmentally Benign ◽  
High Yield ◽  
Carbon Microsphere ◽  
Catalytic Material ◽  
Operational Simplicity

Aim and Objective: The present study was performed with the aim to develop an efficient and environmentally benign protocol for the synthesis of biologically siginifcant 3, 4-dihydropyrano[c]chromenes using a new catalytic material. The protocol involves the use of a reusable, environment friendly materials and solvents with operational simplicity. Materials and Methods: Carbon microsphere supported copper nanoparticles (Cu-NP/C) prepared from loaded cation exchange resin were synthesized, characterized with well versed analytical techniques such as XRD, SEM and Raman spectroscopy and the synthesized material was used as a catalyst for the environmentally benign synthesis of 3,4-dihydropyrano[c]chromenes. Results: The formation of carbon microsphere supported copper nanoparticles (Cu-NP/C) prepared from loaded cation exchange resin was confirmed by XRD, SEM and Raman spectroscopy which was employed as a heterogeneous material for the synthesis of 3,4-dihydropyrano[c]chromenes. The products formed were characterized by the analysis of spectroscopic data - NMR, IR and mass. The safe catalytic system offers several advantages including operational simplicity, environmental friendliness, high yield, and reusability of catalyst and green chemical transformation. Conclusion: Herein we report an easy and efficient protocol for the one-pot synthesis of dihydropyrano[ c]chromenes using environmentally benign MCR approach in ethanol as the green solvent. The method developed herein constitutes a valuable addition to the existing methods for the synthesis of titled compounds.

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