Work

A new one-pot microwave-assisted synthesis and structural analysis of 6,N2,N4-trisubstituted 1,3,5-triazine-2,4-diamines

Year: 2024

Type: article

Abstract: The substituted 1,3,5-triazine-2,4-diamine motif is a well-recognised scaffold for the construction of bioactive compounds. To improve the synthetic accessibility of these compounds and expand their molecular diversity, a convenient one-pot, two-step method for the synthesis of 6, N 2 , N 4 -trisubstituted 1,3,5-triazine-2,4-diamines was developed. The three-component acid-catalysed reaction of arylaldehydes, amines, and N -arylcyanoguanidines under microwave irradiation resulted in the dihydrotriazine ring closure. The subsequent microwave irradiation of the reaction mixture after treatment with a base afforded fully aromatic 6, N 2 , N 4 -trisubstituted 1,3,5-triazine-2,4-diamines as products of dehydrogenative aromatisation. The method was rather general, tolerated structural variations of all reactants and afforded a high chemical diversity of products. The molecular structure and intermolecular interactions in the crystal of N 2 -phenyl-4-morpholino-6-(4-methylphenyl)-1,3,5-triazine-2-amine as a representative example were studied using X-ray crystallography and molecular Hirshfeld surface analysis. The crystal packing was stabilised by two one-dimensional motifs: hydrogen bonding between the secondary amino group and morpholine moiety oxygen and π⋅⋅⋅π stacking interactions, common for the electron-deficient 1,3,5-triazine ring.

Source: Journal of Molecular Structure

DOI: 10.1016/j.molstruc.2024.140965

Authors: Han Yin Lim, Yee Seng Tan, Chien Ing Yeo, Anton V. Dolzhenko

Institutions: Monash University Malaysia, Sunway University, Curtin University

Language: English

Topic: Synthesis and Characterization of Heterocyclic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,570

Funders: Ministry of Higher Education, Malaysia, Monash University Malaysia