Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie
The synthesis of seven-membered benzo-1,3,4-oxadiazepines can be carried out through one-step intramolecular cyclization of N-(2-hydroxybenzoyl)hydrazones. The reaction was catalyzed by 4.50% (v/v) of sulfuric acid in acetic anhydride (Vt = 1 mL) at room temperature. The catalytic and substituent ef...
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| Format: | Thesis |
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2018
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| Online Access: | http://studentsrepo.um.edu.my/9617/ http://studentsrepo.um.edu.my/9617/1/Chan_Pei_Qie.pdf http://studentsrepo.um.edu.my/9617/9/pei_qie.pdf |
| _version_ | 1848773965807353856 |
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| author | Chan, Pei Qie |
| author_facet | Chan, Pei Qie |
| author_sort | Chan, Pei Qie |
| building | UM Research Repository |
| collection | Online Access |
| description | The synthesis of seven-membered benzo-1,3,4-oxadiazepines can be carried out through one-step intramolecular cyclization of N-(2-hydroxybenzoyl)hydrazones. The reaction was catalyzed by 4.50% (v/v) of sulfuric acid in acetic anhydride (Vt = 1 mL) at room temperature. The catalytic and substituent effects on the reactivity of this intramolecular cyclization were investigated. Through this strategy, a series of benzo-1,3,4-oxadiazepine derivatives were prepared (with yield up to 83%). These new heterocyclic compounds were characterized through their melting point, NMR and HRMS (ESI). It was observed that when electron-withdrawing group is at the para position of salicylic ring and electron-donating group at the para position of benzylidene ring, a good yield of seven-membered benzoxadiazepines were obtained. This strategy provided good method to a variety of substitution. |
| first_indexed | 2025-11-14T13:50:47Z |
| format | Thesis |
| id | um-9617 |
| institution | University Malaya |
| institution_category | Local University |
| last_indexed | 2025-11-14T13:50:47Z |
| publishDate | 2018 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | um-96172021-01-20T20:59:10Z Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie Chan, Pei Qie Q Science (General) QD Chemistry The synthesis of seven-membered benzo-1,3,4-oxadiazepines can be carried out through one-step intramolecular cyclization of N-(2-hydroxybenzoyl)hydrazones. The reaction was catalyzed by 4.50% (v/v) of sulfuric acid in acetic anhydride (Vt = 1 mL) at room temperature. The catalytic and substituent effects on the reactivity of this intramolecular cyclization were investigated. Through this strategy, a series of benzo-1,3,4-oxadiazepine derivatives were prepared (with yield up to 83%). These new heterocyclic compounds were characterized through their melting point, NMR and HRMS (ESI). It was observed that when electron-withdrawing group is at the para position of salicylic ring and electron-donating group at the para position of benzylidene ring, a good yield of seven-membered benzoxadiazepines were obtained. This strategy provided good method to a variety of substitution. 2018-07 Thesis NonPeerReviewed application/pdf http://studentsrepo.um.edu.my/9617/1/Chan_Pei_Qie.pdf application/pdf http://studentsrepo.um.edu.my/9617/9/pei_qie.pdf Chan, Pei Qie (2018) Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie. Masters thesis, University of Malaya. http://studentsrepo.um.edu.my/9617/ |
| spellingShingle | Q Science (General) QD Chemistry Chan, Pei Qie Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title | Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title_full | Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title_fullStr | Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title_full_unstemmed | Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title_short | Facile intramolecular cyclization of N-(2 hydroxybenzoyl) hydrazones to N,N'-diacetyl benzo-1,3,4-oxadiazepine derivatives / Chan Pei Qie |
| title_sort | facile intramolecular cyclization of n-(2 hydroxybenzoyl) hydrazones to n,n'-diacetyl benzo-1,3,4-oxadiazepine derivatives / chan pei qie |
| topic | Q Science (General) QD Chemistry |
| url | http://studentsrepo.um.edu.my/9617/ http://studentsrepo.um.edu.my/9617/1/Chan_Pei_Qie.pdf http://studentsrepo.um.edu.my/9617/9/pei_qie.pdf |