Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin

Unsaturated pyrrolidinone has been extensively studied due to its unique structure and its presence in various biologically active natural compounds. In this study, 3- pyrrolin-2 -one, 162 has been constructed via five steps which included condensation of glycine methyl ester and methyl malonyl chl...

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Main Author:	Saaidin, Aimi Suhaily
Format:	Thesis
Language:	English
Published:	2015
Subjects:	QD Chemistry Theory of solution
Online Access:	http://ir.uitm.edu.my/id/eprint/13847/ http://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf

id	uitm-13847
recordtype	eprints
spelling	uitm-138472016-05-14T07:16:39Z http://ir.uitm.edu.my/id/eprint/13847/ Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin Saaidin, Aimi Suhaily QD Chemistry Theory of solution Unsaturated pyrrolidinone has been extensively studied due to its unique structure and its presence in various biologically active natural compounds. In this study, 3- pyrrolin-2 -one, 162 has been constructed via five steps which included condensation of glycine methyl ester and methyl malonyl chloride, Dieckmann cyclization, decarbomethoxylation, reduction and elimination with an overall yield of 33%. The synthesized compound 162 was then used as the intermediate for a few chemical transformations such as Michael addition and epoxidation reaction. Synthesis of fused bicyclic 3,4-y-lactone-y-lactam towards mescaline isocitrimide was also attempted. The synthetic approach was divided into two different routes. The first route began by insertion of dimethyl malonate onto the synthesized intermediate of 3 pyrrolin-2 -one via Michael addition reaction, followed by methylation of the P-diester and bromination at C3 position. However, the bromination reaction failed to give us the desired product which then diverted us to the second route. In this route, the y-lactoney- lactam ring system was successfully synthesized by coupling readily available benzylated glycine methyl ester and methyl malonyl chloride followed by Dieckmann cyclization, alkylation at C3 position and Krapcho decarboxylation. The fused bicyclic ring was afforded through stereoselective reduction which accompanied concomitant lactonization with an overall yield of 0.8%. In brief, we have developed an operationally simple procedure towards the synthesis of 3-pyrrolin-2-one and fused bicyclic 3,4-y-lactone-y-lactam ring skeleton. The results extracted from this study thus far may be used to develop new scientific knowledge and remarkable findings. 2015 Thesis NonPeerReviewed text en http://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf Saaidin, Aimi Suhaily (2015) Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin. 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	QD Chemistry Theory of solution
spellingShingle	QD Chemistry Theory of solution Saaidin, Aimi Suhaily Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
description	Unsaturated pyrrolidinone has been extensively studied due to its unique structure and its presence in various biologically active natural compounds. In this study, 3- pyrrolin-2 -one, 162 has been constructed via five steps which included condensation of glycine methyl ester and methyl malonyl chloride, Dieckmann cyclization, decarbomethoxylation, reduction and elimination with an overall yield of 33%. The synthesized compound 162 was then used as the intermediate for a few chemical transformations such as Michael addition and epoxidation reaction. Synthesis of fused bicyclic 3,4-y-lactone-y-lactam towards mescaline isocitrimide was also attempted. The synthetic approach was divided into two different routes. The first route began by insertion of dimethyl malonate onto the synthesized intermediate of 3 pyrrolin-2 -one via Michael addition reaction, followed by methylation of the P-diester and bromination at C3 position. However, the bromination reaction failed to give us the desired product which then diverted us to the second route. In this route, the y-lactoney- lactam ring system was successfully synthesized by coupling readily available benzylated glycine methyl ester and methyl malonyl chloride followed by Dieckmann cyclization, alkylation at C3 position and Krapcho decarboxylation. The fused bicyclic ring was afforded through stereoselective reduction which accompanied concomitant lactonization with an overall yield of 0.8%. In brief, we have developed an operationally simple procedure towards the synthesis of 3-pyrrolin-2-one and fused bicyclic 3,4-y-lactone-y-lactam ring skeleton. The results extracted from this study thus far may be used to develop new scientific knowledge and remarkable findings.
format	Thesis
author	Saaidin, Aimi Suhaily
author_facet	Saaidin, Aimi Suhaily
author_sort	Saaidin, Aimi Suhaily
title	Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
title_short	Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
title_full	Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
title_fullStr	Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
title_full_unstemmed	Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin
title_sort	chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / aimi suhaily saaidin
publishDate	2015
url	http://ir.uitm.edu.my/id/eprint/13847/ http://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf
first_indexed	2023-09-18T22:50:24Z
last_indexed	2023-09-18T22:50:24Z
_version_	1777417505359265792

Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin

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