Arylated beta-dicarbonyl compounds and process for the preparation thereof
AssigneeCouncil of Scientific and Industrial Research
InventorsMhaske Baburao Santosh, Ranjeet Ashokrao Dhokale, Pramod Rameshrao Thakare
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Abstract
The invention discloses a one pot process for the arylation of β-dicarbonyl compounds. Particularly, the present invention discloses transition-metal-free, chemo-selective, one pot process for the C-arylation of malonamide esters having Formula I at room temperature provide temperature range to obtain the arylated compounds of formula II with good yield, wherein the arylated compounds are selected from mono-arylated compound and di-arylated compound or mixture thereof.
Claims10
A compound of formula II
- wherein R1 and R2 is independently selected from the group consisting of hydrogen,substituted or unsubstituted alkyl such as (C1-C14)alkyl;
- substituted or unsubstituted aryl such as phenyl, halo phenyl, alkoxy phenyl, alkyl phenyl, nitro phenyl;
- benzyl, heterocyclic compound;
- and
- R3=H, alkyl, benzyl or Ar;
- Ar is selected from phenyl;
- halo substituted phenyl wherein halo group is selected from fluro, chloro or bromo;
- alkyl substituted phenyl wherein alkyl is methyl, ethyl, propyl or butyl.
A one pot, process for C-arylation of β-dicarbonyl compounds of Formula I at temperature in the range of 20 to 30° C. comprising the steps of:
- i. reacting benzyne precursor with compound of formula I in the ratio ranging between 1:1 to 1:8 in presence of 0.5 to 5 molar concentration solvent, and fluoride source to obtain a reaction mixture;
- ii. concentrating reaction mixture as obtained in step (a) in vacuo followed by purifying to obtain compound of formula II yielding in the range of 40-97%.
- wherein R1 and R2 is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl such as (C1-C14)alkyl;
- substituted or unsubstituted aryl such as phenyl, halo phenyl, alkoxy phenyl, alkyl phenyl, nitro phenyl;
- benzyl, heterocyclic compound;
- R3=Ar or H;
- and
- Ar is selected from phenyl;
- halo substituted phenyl wherein halo group is selected from fluro, chloro or bromo;
- alkyl substituted phenyl wherein alkyl is selected from methyl, ethyl, propyl or butyl.
Dependencies are inferred from the claim text.