A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines
An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5] triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide...
| Main Authors: | , , , , , |
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| Format: | Journal Article |
| Published: |
Royal Society of Chemistry
2017
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| Online Access: | http://hdl.handle.net/20.500.11937/59385 |
| _version_ | 1848760465904107520 |
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| author | Lim, F. Low, S. Ho, E. Halcovitch, N. Tiekink, E. Dolzhenko, Anton |
| author_facet | Lim, F. Low, S. Ho, E. Halcovitch, N. Tiekink, E. Dolzhenko, Anton |
| author_sort | Lim, F. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5] triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible i n three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction. |
| first_indexed | 2025-11-14T10:16:13Z |
| format | Journal Article |
| id | curtin-20.500.11937-59385 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T10:16:13Z |
| publishDate | 2017 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-593852018-03-29T03:39:58Z A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines Lim, F. Low, S. Ho, E. Halcovitch, N. Tiekink, E. Dolzhenko, Anton An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5] triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible i n three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction. 2017 Journal Article http://hdl.handle.net/20.500.11937/59385 10.1039/c7ra11305f Royal Society of Chemistry unknown |
| spellingShingle | Lim, F. Low, S. Ho, E. Halcovitch, N. Tiekink, E. Dolzhenko, Anton A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title | A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title_full | A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title_fullStr | A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title_full_unstemmed | A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title_short | A multicomponent reaction of 2-aminoimidazoles: Microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| title_sort | multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7-deaza-adenines |
| url | http://hdl.handle.net/20.500.11937/59385 |