Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor

Mansor, Nurul Shulehaf (2014) Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor. Masters thesis, Universiti Teknologi MARA.

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Abstract

Nitrogen containing heterocycles have attracted the interest of many research groups because they are widely found in nature as well as in pharmaceutical products. However, the syntheses of pyrrolidine-2,3-dione are rarely reported. In this study, 2,3- dioxo-4-carboxy-5-(substituted)pyrrolidines were synthesized to be potential intermediates for bioactive compounds. The key step in the synthetic strategy towards pyrrolidine-2,3-dione was the multicomponent reactions (MCR’s) using sodium diethyl oxalacetate, various amines and aldehydes as the starting materials. Using this protocol, a series of 2,3-dioxo-4-carboxy-5-(aromatic or aliphatic)pyrrolidines were successfully produced in moderate to good yields. In similar investigation, a chiral amine, (^-phenyl ethyl amine was employed in order to confirm the stereochemistry of the functionality at the C-5 position of the pyrrolidine skeleton. Compound pyrrolidine-2,3-dione was then used as the intermediate for a few chemical transformations including the synthesis of C-4 alkylated compound which can be the advanced precursor for (Z)-pulchellalactam. Synthesis of novel y-lactam p-lactone bicyclic ring and (-)-codonopsinine anologue, a-haloketo pyrrolidine were also attempted in other chemical transformations using pyrrolidine-2,3-dione as the intermediate. The chemical reactions employed to synthesize these target compounds were alkylation, stereoselective reduction, hydrolysis, decarboxylation, a-keto halogenation, O-protection and epoxidation. Therefore, via these various chemical reactions, over 40 pyrrolidinone type compounds have been successfully synthesized and 25 were identified as novel compounds. In summary, a few novel synthetic approaches towards the synthesis of some pyrrolidine type compounds of biological importance were devised using intermediate of 2,3-dixo-4carboxy-5- (substituted)pyrrolidine. Results extracted from this study might be used to develop new scientific knowledge and remarkable findings.

Item Type: Thesis (Masters)
Creators:
CreatorsEmail
Mansor, Nurul ShulehafUNSPECIFIED
Subjects: Q Science > QH Natural history - Biology > Bioactive compounds
R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculty of Applied Sciences
Item ID: 14296
Uncontrolled Keywords: Nitrogen; Pharmaceutical products; Pyrrolidine-2,3-dione
Last Modified: 24 Aug 2016 08:48
Depositing User: Staf Pendigitalan 2
URI: http://ir.uitm.edu.my/id/eprint/14296

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