Production of furanones
AssigneeUnisearch Limited, A.C.N.
InventorsRoger Read, Naresh Kumar
Life of this patent
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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, carboxylate and sulfinate and sulfonate esters, ethers, aldehydes, ketones, acids, amides, nitro derivatives, hydrophobic, hydrophilic and fluorophilic alkyl derivatives and a polymers.
Claims9
A compound according to formula (III):
- wherein R2 and R3 are independently or both hydrogen or halogen;
- R5 is OH, hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl aryl or arylalkyl;
- R9 is halogen;
- wherein each substituent can be substituted or unsubstituted, straight chain or branched chain.
A compound according to formula (IV) or (V):
- wherein R1 is hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl;
- R2 and R3 are independently or both hydrogen or halogen;
- R9 is halogen;
- R8 is OH, NHR1, NHC(X)NH2, NHC(X)NHR1 or R1 where X is O, S or NR1;
- and
- wherein each substituent can be substituted or unsubstituted, straight chain or branched chain.
A method for forming a compound of formula (III), comprising reacting a compound of the following formula
- with an oxidising agent to form the compound in accordance with formula (III):
- wherein R2 and R3 are independently or both hydrogen or halogen;
- R5 is OH, hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl;
- R9 is halogen;
- and wherein each substituent can be substituted or unsubstituted, straight chain or branched chain.
A method for forming a compound of formula (IV) or (V), comprising reacting an aldehyde or ketone substituent in the side chain —C(O)R5 of compound (III) with an amine to form a compound of formula (IV) or (V),
- wherein formula (IV) and (V) are represented by:
- wherein R1 is hydrogen, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl;
- R2 and R3 are independently or both hydrogen or halogen;
- R9 is halogen;
- R8 is OH, NHR1, NHC(X)NH2, NHC(X)NHR1 or R1 where X is O, S or NR1;
- and
- wherein each substituent can be substituted or unsubstituted, straight chain or branched chain;
- and wherein formula (III) is represented by:
- wherein R2 and R3 are independently or both hydrogen or halogen;
- R5 is OH or the same as R1;
- and
- R9 is halogen.
A compound of formula (VI):
- wherein R1 is alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl;
- R2 and R3 are independently or both hydrogen or halogen;
- R9 is halogen;
- and
- wherein each substituent can be substituted or unsubstituted, straight chain or branched chain.
Dependencies are inferred from the claim text.