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...
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| Format: | Article |
| Language: | English |
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Royal Society of Chemistry
2017
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| Online Access: | http://eprints.sunway.edu.my/712/ http://eprints.sunway.edu.my/712/1/Tiekink%20A%20multicomponent%20RSC%20Adv%202017%20.pdf |
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| author | Lim, Felicia Phei Lin Low, Szy Teng Ho, Elvina Lee King Halcovitch, Nathan R. Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_facet | Lim, Felicia Phei Lin Low, Szy Teng Ho, Elvina Lee King Halcovitch, Nathan R. Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_sort | Lim, Felicia Phei Lin |
| building | SU 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 in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction. |
| first_indexed | 2025-11-14T21:14:32Z |
| format | Article |
| id | sunway-712 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:32Z |
| publishDate | 2017 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-7122020-10-07T09:45:41Z http://eprints.sunway.edu.my/712/ A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7- deaza-adenines†‡ Lim, Felicia Phei Lin Low, Szy Teng Ho, Elvina Lee King Halcovitch, Nathan R. Tiekink, Edward R. T. * Dolzhenko, Anton V QD Chemistry 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 in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction. Royal Society of Chemistry 2017 Article PeerReviewed text en http://eprints.sunway.edu.my/712/1/Tiekink%20A%20multicomponent%20RSC%20Adv%202017%20.pdf Lim, Felicia Phei Lin and Low, Szy Teng and Ho, Elvina Lee King and Halcovitch, Nathan R. and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2017) A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7- deaza-adenines†‡. RSC Advances, 7 (81). pp. 51062-51068. ISSN 2046-2069 DOI: 10.1039/c7ra11305f |
| spellingShingle | QD Chemistry Lim, Felicia Phei Lin Low, Szy Teng Ho, Elvina Lee King Halcovitch, Nathan R. Tiekink, Edward R. T. * Dolzhenko, Anton V 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†‡ |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/712/ http://eprints.sunway.edu.my/712/ http://eprints.sunway.edu.my/712/1/Tiekink%20A%20multicomponent%20RSC%20Adv%202017%20.pdf |