Production of Furanones
AssigneeUnisearch Limited, A.C.N.
InventorsRoger Read, Naresh Kumar
Life of this patent
Estimating the term…
Abstract
The present invention relates to the side chain functionalization of fimbrolides (halogenated 3-alkyl-5-methylene-2(5H)-furanones) and their synthetic analogues, that yields fimbrolides substituted with a halogen, an oxygen or a nitrogen functionality in the alkyl chain, especially fimbrolide alcohols, caboxylate and sulfinate and sulfonate esters, ethers, aldehydes, ketones, acids, amides, nitro derivatives, hydrophobic, hydrophilic and fluorophilic alkyl derivatives and polymers.
Claims16
1-26. (canceled)
A method for forming a fimbrolide derivative, the method including reacting a fimbrolide with a halogenating agent and/or an oxygenating agent to form compounds with formula (Ia):
- wherein R1 is hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl whether unsubstituted or substituted, straight chain or branched chain, hydrophobic, hydrophilic or fluorophilic;
- X is a halogen (X═F, Cl, Br or I), OH, OOH, OC(O)R1 or ═O;
- R2 and R3 are independently or both hydrogen or halogen;
- and
- R9 is halogen.
A method for forming a fimbrolide derivative, the method including displacement and/or functionalisation of the halogen or oxygen substituent in the fimbrolide side chain by treating with a nucleophile or an electrophile to form compounds with formula (II):
- wherein R1 is hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl whether unsubstituted or substituted, straight chain or branched chain, hydrophobic, hydrophilic or fluorophilic;
- R2 and R3 are independently or both hydrogen or halogen;
- R9 is halogen;
- and
- R4 is selected from the group halogen, amine, azide, hydroxyl, thiol, or any hydrophobic, hydrophilic or fluorophilic alkyl, alkoxy, mercaptoalkyl, alkenyloxy, mercaptoalkenyl, aryloxy, mercaptoaryl, arylalkyloxy, mercaptoarylalkyl, OC(O)R1, SC(O)R1, OS(O)R1, OS(0)2R1, NHC(O)R1, OC(O)NHR1, or ═O.
A fimbrolide derivative selected from the group consisting of:
Dependencies are inferred from the claim text.