New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization
A new, effective one-pot synthesis of the 6,N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the r...
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American Chemical Society
2019
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| Online Access: | http://eprints.sunway.edu.my/1072/ |
| _version_ | 1848801968496050176 |
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| author | Ahmad Junaid, Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_facet | Ahmad Junaid, Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_sort | Ahmad Junaid, |
| building | SU Institutional Repository |
| collection | Online Access |
| description | A new, effective one-pot synthesis of the 6,N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties. |
| first_indexed | 2025-11-14T21:15:53Z |
| format | Article |
| id | sunway-1072 |
| institution | Sunway University |
| institution_category | Local University |
| last_indexed | 2025-11-14T21:15:53Z |
| publishDate | 2019 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-10722020-10-07T08:36:53Z http://eprints.sunway.edu.my/1072/ New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization Ahmad Junaid, Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V QD Chemistry A new, effective one-pot synthesis of the 6,N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties. American Chemical Society 2019-06-10 Article PeerReviewed Ahmad Junaid, and Lim, Felicia Phei Lin and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2019) New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization. ACS Combinatorial Science, 21 (7). pp. 548-555. ISSN 2156 8952 https://pubs.acs.org/doi/full/10.1021/acscombsci.9b00079 |
| spellingShingle | QD Chemistry Ahmad Junaid, Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title | New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title_full | New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title_fullStr | New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title_full_unstemmed | New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title_short | New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization |
| title_sort | new one-pot synthesis of 1,3,5-triazines: three-component condensation, dimroth rearrangement, and dehydrogenative aromatization |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1072/ http://eprints.sunway.edu.my/1072/ |