Practical One-Pot Synthesis of 4,6-Bis(hetero)aryl- and 4-(Hetero) aryl-6-methyl-substituted 1,3,5-Triazin-2-amines

Laís C. Calheiros; Sidnei Moura; Davi F. Back; Guilherme C. Paveglio; Gleison A. Casagrande; Lucas Pizzuti

doi:10.1055/a-1970-8229

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(07): 1130-1138
DOI: 10.1055/a-1970-8229

paper

Practical One-Pot Synthesis of 4,6-Bis(hetero)aryl- and 4-(Hetero) aryl-6-methyl-substituted 1,3,5-Triazin-2-amines

Laís C. Calheiros

^aGrupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

^bLaboratorio de Síntese de Substâncias Bioativas, CINPROBIO-CLF, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

,

Sidnei Moura

^cLaboratório de Biotecnologia de Produtos Naturais e Sintéticos, Universidade de Caxias do Sul, 95070-560 Caxias do Sul (RS), Brazil

,

Davi F. Back

^dLaboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, 97105-900 Santa Maria (RS), Brazil

,

Guilherme C. Paveglio∗

^aGrupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

^bLaboratorio de Síntese de Substâncias Bioativas, CINPROBIO-CLF, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

,

Gleison A. Casagrande∗

^eGrupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande (MS), Brazil

,

Lucas Pizzuti ∗

^aGrupo de Pesquisa em Síntese e Caracterização Molecular do Mato Grosso do Sul, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

^bLaboratorio de Síntese de Substâncias Bioativas, CINPROBIO-CLF, Universidade Federal da Grande Dourados, 79825-070 Dourados (MS), Brazil

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Abstract

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Abstract

Two series of 4,6-disubstituted 1,3,5-triazin-2-amines were prepared by cesium carbonate-promoted cotrimerization of aromatic nitriles with guanidine and the reaction of (hetero)aryl nitriles with N-acetylguanidine. The first series of 4,6-bis(hetero)aryl-1,3,5-triazin-2-amines was synthesized in yields of 56–85% by adapting a traditional approach that starts from readily available substrates but requires strong and hard-to-handle bases as well as presents serious scope limitations. In this line, the method developed here used a mild base and overcame the scope limitation for p-substituted benzonitrile with electron-releasing group. The second series of 4-(hetero)aryl-6-methyl-1,3,5-triazin-2-amines comprises unsymmetrically substituted symmetrical triazines, which were synthesized in yields of 58–75%. In summary, this work highlighted a synthetic method, which tolerates broad range of substrates, including o- and p-substituted benzonitriles as well as heteroaromatic nitriles.

Key words

symmetrical triazines - heterocycles - cotrimerization reactions - guanidine - cesium carbonate

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