Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione
A synthesis of hitherto unknown heterocyclic system 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (5) is presented. The cyclocondensation of 2,6-diaminopyridine (1) with maleic anhydride yielded (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acid (2), which was converted to methyl (5-amino-...
| Main Authors: | , , |
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| Format: | Journal Article |
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The Japan Institute of Heterocyclic Chemistry
2007
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| Online Access: | http://hdl.handle.net/20.500.11937/19549 |
| _version_ | 1848750064490512384 |
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| author | Dolzhenko, Anton Dolzhenko, A. Chui, W. |
| author_facet | Dolzhenko, Anton Dolzhenko, A. Chui, W. |
| author_sort | Dolzhenko, Anton |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | A synthesis of hitherto unknown heterocyclic system 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (5) is presented. The cyclocondensation of 2,6-diaminopyridine (1) with maleic anhydride yielded (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acid (2), which was converted to methyl (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl) acetate hydrochloride (3). The ester (3) upon treatment with sodium carbonate solution underwent intramolecular cyclization to 2a,3-dihydro-1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (4), which was oxidized in alkaline condition to provide 5. |
| first_indexed | 2025-11-14T07:30:53Z |
| format | Journal Article |
| id | curtin-20.500.11937-19549 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T07:30:53Z |
| publishDate | 2007 |
| publisher | The Japan Institute of Heterocyclic Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-195492017-01-30T12:14:30Z Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione Dolzhenko, Anton Dolzhenko, A. Chui, W. A synthesis of hitherto unknown heterocyclic system 1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (5) is presented. The cyclocondensation of 2,6-diaminopyridine (1) with maleic anhydride yielded (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)acetic acid (2), which was converted to methyl (5-amino-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl) acetate hydrochloride (3). The ester (3) upon treatment with sodium carbonate solution underwent intramolecular cyclization to 2a,3-dihydro-1(5)H-1,5-diazacycl[3.3.2]azine-2,4-dione (4), which was oxidized in alkaline condition to provide 5. 2007 Journal Article http://hdl.handle.net/20.500.11937/19549 The Japan Institute of Heterocyclic Chemistry fulltext |
| spellingShingle | Dolzhenko, Anton Dolzhenko, A. Chui, W. Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title | Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title_full | Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title_fullStr | Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title_full_unstemmed | Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title_short | Synthesis of New Heterocyclic System: 1(5)H-1,5-Diazacycl[3.3.2]azine-2,4-dione |
| title_sort | synthesis of new heterocyclic system: 1(5)h-1,5-diazacycl[3.3.2]azine-2,4-dione |
| url | http://hdl.handle.net/20.500.11937/19549 |