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

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 wer...

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Main Author:	Mansor, Nurul Shulehaf
Format:	Thesis
Language:	English
Published:	2014
Subjects:	Bioactive compounds
Online Access:	https://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf
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spelling	my-uitm-ir.142962022-04-01T08:20:53Z Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor 2014-06 Mansor, Nurul Shulehaf Bioactive compounds RM Therapeutics. Pharmacology 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. 2014-06 Thesis https://ir.uitm.edu.my/id/eprint/14296/ https://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf text en public mphil masters Universiti Teknologi MARA Faculty of Applied Sciences Mohammat @ M.yahya, Mohd Fazli (Dr) Hamzah, Ahmad Sazali (Prof. Dr.)
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Mohammat @ M.yahya, Mohd Fazli (Dr) Hamzah, Ahmad Sazali (Prof. Dr.)
topic	Bioactive compounds Bioactive compounds
spellingShingle	Bioactive compounds Bioactive compounds Mansor, Nurul Shulehaf Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
description	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.
format	Thesis
qualification_name	Master of Philosophy (M.Phil.)
qualification_level	Master's degree
author	Mansor, Nurul Shulehaf
author_facet	Mansor, Nurul Shulehaf
author_sort	Mansor, Nurul Shulehaf
title	Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
title_short	Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
title_full	Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
title_fullStr	Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
title_full_unstemmed	Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor
title_sort	synthetic studies of some pyrrolidine-2,3-dione type compounds / nurul shulehaf mansor
granting_institution	Universiti Teknologi MARA
granting_department	Faculty of Applied Sciences
publishDate	2014
url	https://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf
_version_	1783733247851626496

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

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