A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation
A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochlor...
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| Format: | Article |
| Language: | English |
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2021
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| Online Access: | http://eprints.sunway.edu.my/1797/ http://eprints.sunway.edu.my/1797/1/Tiekink%20New%20one%20pot%20Accepted%20version.pdf |
| _version_ | 1848802136774672384 |
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| author | Muhammad Syafiq, S Ahmad Junaid, Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_facet | Muhammad Syafiq, S Ahmad Junaid, Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_sort | Muhammad Syafiq, S |
| building | SU Institutional Repository |
| collection | Online Access |
| description | A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) to the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-(3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)-4-phenyl-1,3,5-triazin-2-amine. |
| first_indexed | 2025-11-14T21:18:33Z |
| format | Article |
| id | sunway-1797 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:18:33Z |
| publishDate | 2021 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-17972021-07-30T09:49:16Z http://eprints.sunway.edu.my/1797/ A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation Muhammad Syafiq, S Ahmad Junaid, Tiekink, Edward R. T. * Dolzhenko, Anton V QD Chemistry A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) to the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-(3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)-4-phenyl-1,3,5-triazin-2-amine. 2021 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1797/1/Tiekink%20New%20one%20pot%20Accepted%20version.pdf Muhammad Syafiq, S and Ahmad Junaid, and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2021) A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation. Synthesis, 53 (14). pp. 2457-2468. ISSN 0039-7881 http://doi.org/10.1055/a-1401-2795 doi:10.1055/a-1401-2795 |
| spellingShingle | QD Chemistry Muhammad Syafiq, S Ahmad Junaid, Tiekink, Edward R. T. * Dolzhenko, Anton V A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title | A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title_full | A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title_fullStr | A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title_full_unstemmed | A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title_short | A New one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| title_sort | new one-pot three-component synthesis of 4-aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1797/ http://eprints.sunway.edu.my/1797/ http://eprints.sunway.edu.my/1797/ http://eprints.sunway.edu.my/1797/1/Tiekink%20New%20one%20pot%20Accepted%20version.pdf |