New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization

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

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: triazines, multicomponent reactions, microwave-assisted synthesis, anticancer activity
Subjects: Q Science > QD Chemistry
Divisions: Sunway University > School of Science and Technology > Research Centre for Crystalline Materials
Others > Non Sunway Academics
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 15 Jul 2019 01:39
Last Modified: 15 Jul 2019 01:39
URI: http://eprints.sunway.edu.my/id/eprint/1072

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