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 RM Therapeutics. Pharmacology
Online Access:	http://ir.uitm.edu.my/id/eprint/14296/ http://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf

id	uitm-14296
recordtype	eprints
spelling	uitm-142962016-08-24T08:48:38Z http://ir.uitm.edu.my/id/eprint/14296/ Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor 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 Thesis NonPeerReviewed text en http://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf Mansor, Nurul Shulehaf (2014) Synthetic studies of some Pyrrolidine-2,3-dione type compounds / Nurul Shulehaf Mansor. Masters thesis, Universiti Teknologi MARA.
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Teknologi MARA
building	UiTM Institutional Repository
collection	Online Access
language	English
topic	Bioactive compounds RM Therapeutics. Pharmacology
spellingShingle	Bioactive compounds RM Therapeutics. Pharmacology 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
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
publishDate	2014
url	http://ir.uitm.edu.my/id/eprint/14296/ http://ir.uitm.edu.my/id/eprint/14296/1/TM_NURUL%20SHULEHAF%20MANSOR%20AS%2014_5.pdf
first_indexed	2023-09-18T22:51:18Z
last_indexed	2023-09-18T22:51:18Z
_version_	1777417561958252544

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

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