Functionalized Maleimides and Isomaleimides and a process for preparation thereof
AssigneeCouncil of Scientific and Industrial Research
InventorsSantosh Baburao Mhaske, Amol Basagonda Viveki, Mahesh Dattatraya Pol
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Abstract
The present invention relates to functionalized Maleimides and Isomaleimides of general Formula (I) and a process for the preparation thereof, involving [3+2] annulation of α, β-unsaturated aldehydes with carbamoyl alkylates via an enolate pathway to afford highly functionalized compounds of Formula (I);
Claims16
A functionalized maleimide and isomaleimide of Formula (I):
- wherein, X and Y independently of each other represent heteroatom selected from nitrogen or oxygen;
- R1, R2, and R3 independently of each other represent unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted carbocycle, unsubstituted or substituted benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl;
- R4 independently of each other represent hydrogen or C1-4 alkyl,
- ‘n’ is the integer 1 to 9;
- ‘p’ is the integer 1to 2 with the proviso,
- when ‘X’ is oxygen, ‘Y’ is nitrogen and R1 is absent;
- when ‘Y’ is oxygen, ‘X’ is nitrogen and R2 is absent;
- when ‘p’ is 2, the compound is a bisimide or its congeners at R2;
- excluding the compounds wherein,
- ‘X’, ‘Y’, are oxygen, R1 and R2 are absent, R3 is methyl, ‘m’ is the integer 1, ‘n’ is the integer 5 and R4 is hydrogen;
- ‘X’ is nitrogen, ‘Y is oxygen, R1 is p-tolyl, R3 is methyl, ‘m’ is the integer 1, ‘n’ is the integer 5 and R4 is ethyl.
A process for preparation of functionalized maleimide and isomaleimide of Formula (I), wherein the process comprises:
- reacting N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation of α,β-unsaturated aldehydes of Formula (II), with carbamoyl alkylates of Formula (III) in presence of NHC precursors, a base, and a solvent to obtain compounds of Formula (I);
- wherein R3 in Formula (II) independently of each other represent the groups selected from unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted carbocycle, unsubstituted or substituted benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl;
- and
- ‘n’ represents the integer 1 to 9;
- wherein R1 or R2 in Formula (III) represent the groups selected from unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted carbocycle, unsubstituted or substituted benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl;
- and
- R4 in Formula (III) represents hydrogen or C1-4 alkyl.
A pharmaceutical composition containing functionalized maleimides and isomaleimides of Formula (I) together with at least one acceptable excipient.
Dependencies are inferred from the claim text.