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Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali

In this study, the development of synthetic strategy towards the formation of fused heterocyclic-y-lactam rings system containing oxygen and/ or nitrogen atom were successfully established. The key intermediate y-lactam or 2,3-pyrrolidinedione ring template was effectively constructed using a multic...

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Main Author: Rezali, Nurul Syafiqah
Format: Book Section
Language:English
Published: Institute of Graduate Studies, UiTM 2018
Subjects:
Organic chemistry
Online Access:http://ir.uitm.edu.my/id/eprint/22089/1/ABS_NURUL%20SYAFIQAH%20REZALI%20TDRA%20VOL%2014%20IGS%2018.pdf
http://ir.uitm.edu.my/id/eprint/22089/
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spelling my.uitm.ir.220892018-11-13T08:32:05Z http://ir.uitm.edu.my/id/eprint/22089/ Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali Rezali, Nurul Syafiqah Organic chemistry In this study, the development of synthetic strategy towards the formation of fused heterocyclic-y-lactam rings system containing oxygen and/ or nitrogen atom were successfully established. The key intermediate y-lactam or 2,3-pyrrolidinedione ring template was effectively constructed using a multicomponent reaction (MCR) approach utilizing primary amine, aldehyde and diethyl oxalacetate sodium salt in ethanolic medium. The y-lactam ring compound formed exists in the more stable enol form and also appears as racemic mixture. Following this, functional group interconversion of this highly functionalized compound leads to the formation of seven new fused heterocyclic-y-lactam rings system. The fused 5-lactam-y-lactam was effectively constructed via Leuckart reaction, condensation, hydrogenation and Dieckmann cyclisation. The synthesis of fused y-lactam-y-lactam however, involves decarboxylation, insertion of ethyl acetyl group via enamine-chemistry, imine formation and hydrogenation followed by an intramolecular cyclisation. The stereoselective reduction of the ethyl acetylic product followed by ester hydrolysis and lactonization via acid activation protocol was successfully carried out to furnish the fused y-lactone-y-lactam compound… Institute of Graduate Studies, UiTM 2018 Book Section PeerReviewed text en http://ir.uitm.edu.my/id/eprint/22089/1/ABS_NURUL%20SYAFIQAH%20REZALI%20TDRA%20VOL%2014%20IGS%2018.pdf Rezali, Nurul Syafiqah (2018) Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali. In: The Doctoral Research Abstracts. IGS Biannual Publication, 14 . Institute of Graduate Studies, UiTM, Shah Alam.
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
topic Organic chemistry
spellingShingle Organic chemistry
Rezali, Nurul Syafiqah
Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
description In this study, the development of synthetic strategy towards the formation of fused heterocyclic-y-lactam rings system containing oxygen and/ or nitrogen atom were successfully established. The key intermediate y-lactam or 2,3-pyrrolidinedione ring template was effectively constructed using a multicomponent reaction (MCR) approach utilizing primary amine, aldehyde and diethyl oxalacetate sodium salt in ethanolic medium. The y-lactam ring compound formed exists in the more stable enol form and also appears as racemic mixture. Following this, functional group interconversion of this highly functionalized compound leads to the formation of seven new fused heterocyclic-y-lactam rings system. The fused 5-lactam-y-lactam was effectively constructed via Leuckart reaction, condensation, hydrogenation and Dieckmann cyclisation. The synthesis of fused y-lactam-y-lactam however, involves decarboxylation, insertion of ethyl acetyl group via enamine-chemistry, imine formation and hydrogenation followed by an intramolecular cyclisation. The stereoselective reduction of the ethyl acetylic product followed by ester hydrolysis and lactonization via acid activation protocol was successfully carried out to furnish the fused y-lactone-y-lactam compound…
format Book Section
author Rezali, Nurul Syafiqah
author_facet Rezali, Nurul Syafiqah
author_sort Rezali, Nurul Syafiqah
title Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
title_short Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
title_full Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
title_fullStr Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
title_full_unstemmed Design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / Nurul Syafiqah Rezali
title_sort design and chemical synthesis of fused 5-, 6oxygen and / or nitrogencontaining heterocyclesg lactam utilizing 2,3-dioxo-4carboxy-5-(substituted) pyrrolidine as the key precursor / nurul syafiqah rezali
publisher Institute of Graduate Studies, UiTM
publishDate 2018
url http://ir.uitm.edu.my/id/eprint/22089/1/ABS_NURUL%20SYAFIQAH%20REZALI%20TDRA%20VOL%2014%20IGS%2018.pdf
http://ir.uitm.edu.my/id/eprint/22089/
_version_ 1685649554173591552
score 13.211869

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