In recent years development of environmentally friendly chemical synthesis is gaining considerable interest in the context of replacement of toxic and volatile organic reagents and solvents as reaction media with environmentally acceptable alternatives such as chemicals from renewable resources (biomass products) are preferable. Polyfunctional molecules that are C-3 natural polyols like glycerol or its derivatives have been proposed as valuable starting materials for synthesis of pharmaceutical compounds and polymers. Glycerol is used as green solvent for catalysis, org. syn., & in materials chemistry, but can also be converted into value-added new chemicals. In this context we have focused our attention on the valorization of glycerol/glycerol derivatives, in green conditions, with or without catalyst/solvent in mild conditions and found that cascade one pot three component reactions of glycerol/glycerol derivatives, dialkyl carbonates with (a) phenols, or (b) amines, and isoserinol with diphenyl carbonate, leads to phenoxy glycerol ethers, alpha-glycerol carbamates, and oxazoidinones respectively, in high yields and with high selectivity. Reaction conditions were optimized. Factors affecting on the selectivity positional and substrate were established based on the steric and linear/cyclic carbonate ester of glycerol/derivatives.
Synthesis of Pharmaceutical Compounds from Biomass Byproducts: Cascade One-Pot Three Component, Solvent Free, Green Reactions
SHISODIA, SURESH UDHAVRAO;CITTERIO, ATTILIO;SEBASTIANO, ROBERTO
2014-01-01
Abstract
In recent years development of environmentally friendly chemical synthesis is gaining considerable interest in the context of replacement of toxic and volatile organic reagents and solvents as reaction media with environmentally acceptable alternatives such as chemicals from renewable resources (biomass products) are preferable. Polyfunctional molecules that are C-3 natural polyols like glycerol or its derivatives have been proposed as valuable starting materials for synthesis of pharmaceutical compounds and polymers. Glycerol is used as green solvent for catalysis, org. syn., & in materials chemistry, but can also be converted into value-added new chemicals. In this context we have focused our attention on the valorization of glycerol/glycerol derivatives, in green conditions, with or without catalyst/solvent in mild conditions and found that cascade one pot three component reactions of glycerol/glycerol derivatives, dialkyl carbonates with (a) phenols, or (b) amines, and isoserinol with diphenyl carbonate, leads to phenoxy glycerol ethers, alpha-glycerol carbamates, and oxazoidinones respectively, in high yields and with high selectivity. Reaction conditions were optimized. Factors affecting on the selectivity positional and substrate were established based on the steric and linear/cyclic carbonate ester of glycerol/derivatives.File | Dimensione | Formato | |
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