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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| Format: | Book Section |
| Language: | English |
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Institute of Graduate Studies, UiTM
2018
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| Online Access: | https://ir.uitm.edu.my/id/eprint/22089/ |
| _version_ | 1848805404029485056 |
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| author | Rezali, Nurul Syafiqah |
| author_facet | Rezali, Nurul Syafiqah |
| author_sort | Rezali, Nurul Syafiqah |
| building | UiTM Institutional Repository |
| collection | Online Access |
| 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… |
| first_indexed | 2025-11-14T22:10:29Z |
| format | Book Section |
| id | uitm-22089 |
| institution | Universiti Teknologi MARA |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T22:10:29Z |
| publishDate | 2018 |
| publisher | Institute of Graduate Studies, UiTM |
| recordtype | eprints |
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| spelling | uitm-220892018-11-13T08:32:05Z https://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 https://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. (2018) In: The Doctoral Research Abstracts. IGS Biannual Publication, 14 . Institute of Graduate Studies, UiTM, Shah Alam. |
| 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 |
| 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_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_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_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 |
| topic | Organic chemistry |
| url | https://ir.uitm.edu.my/id/eprint/22089/ |