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 chlo...

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Main Author:	Saaidin, Aimi Suhaily
Format:	Thesis
Language:	English
Published:	2015
Subjects:	QD Chemistry Theory of solution
Online Access:	https://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf
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id	my-uitm-ir.13847
record_format	uketd_dc
spelling	my-uitm-ir.138472022-04-18T04:19:24Z Chemical studies of 3-pyrrolin-2-one for the synthesis of y-lactam y-lactone / Aimi Suhaily Saaidin 2015-03 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. 2015-03 Thesis https://ir.uitm.edu.my/id/eprint/13847/ https://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf text en public mphil masters Universiti Teknologi MARA Perpustakaan Tun Abdul Razak Hamzah, Ahmad Sazali (Professor Dr.) Haji Shaameri, Zurina (Prof. Madya Dr.)
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Hamzah, Ahmad Sazali (Professor Dr.) Haji Shaameri, Zurina (Prof. Madya Dr.)
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
qualification_name	Master of Philosophy (M.Phil.)
qualification_level	Master's degree
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
granting_institution	Universiti Teknologi MARA
granting_department	Perpustakaan Tun Abdul Razak
publishDate	2015
url	https://ir.uitm.edu.my/id/eprint/13847/1/TM_AIMI%20SUHAILY%20SAAIDIN%20AS%2015_5%201.pdf
_version_	1783733183659900928

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

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