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.

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.

Metadata

Item Type: Thesis (Masters)
Creators:
Creators
Email / ID Num.
Mansor, Nurul Shulehaf
2010965019
Contributors:
Contribution
Name
Email / ID Num.
Thesis advisor
Mohammat @ M.yahya, Mohd Fazli (Dr)
UNSPECIFIED
Thesis advisor
Hamzah, Ahmad Sazali (Prof. Dr.)
UNSPECIFIED
Subjects: Q Science > QH Natural history - Biology > Bioactive compounds
R Medicine > RM Therapeutics. Pharmacology
Divisions: Universiti Teknologi MARA, Shah Alam > Faculty of Applied Sciences
Programme: Master of Science
Keywords: Nitrogen; Pharmaceutical products; Pyrrolidine-2,3-dione
Date: June 2014
URI: https://ir.uitm.edu.my/id/eprint/14296
Edit Item
Edit Item

Download

[thumbnail of TM_NURUL SHULEHAF MANSOR AS 14_5.pdf] Text
TM_NURUL SHULEHAF MANSOR AS 14_5.pdf

Download (1MB)

Digital Copy

Digital (fulltext) is available at:

Physical Copy

Physical status and holdings:
Item Status:

ID Number

14296

Indexing

Statistic

Statistic details