ACYLHYDRAZIDES AS NEW PRECURSORS FOR THE SYNTHESIS OF TRIS-[1,2,4]TRIAZOLO-[1,3,5]-TRIAZINE CORES

Júlia Goes Nunes; Érica Gilioli de Oliveira; Eduard Westphal

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Trabalho

Título do Trabalho

ACYLHYDRAZIDES AS NEW PRECURSORS FOR THE SYNTHESIS OF TRIS-[1,2,4]TRIAZOLO-[1,3,5]-TRIAZINE CORES

Autores

Júlia Goes Nunes
Érica Gilioli de Oliveira
Eduard Westphal

Modalidade

Pôster - resumo

Área temática

Materiais e biomateriais

Data de Publicação

27/05/2026

País da Publicação

Brasil

Idioma da Publicação

pt-BR

Página do Trabalho

https://www.even3.com.br/anais/workshop-do-ineo-2026/1462049-acylhydrazides-as-new-precursors-for-the-synthesis-of-tris-124triazolo-135-triazine-cores

ISBN

978-65-272-2467-9

Palavras-Chave

Heterocycle, Tristriazolotriazine, Organic Synthesis, Triazine, Acylhydrazides

Resumo

The tris-[1,2,4]-triazolo-[1,3,5]-triazine (TTT) core is composed of three 1,2,4-triazole heterocyclic units condensed onto a 1,3,5-triazine, resulting in a planar structure with a high nitrogen content. Since the first report of a phenyl-TTT derivative, in 1961 by Huisgen [1], TTT derivatives have attracted considerable attention due to their promising applicability in liquid crystals [2,3] and luminescent materials [4]. Up to the present moment, TTTs are obtained from the reaction between cyanuric chloride and a tetrazole derivative [1–4], whose formation is limited and involves the use of azide, a hazardous reagent. Therefore, the development of new methodologies is crucial for expanding the library of TTT-derived molecules. In the search for a new synthetic methodology, it was found that replacing tetrazoles with hydrazides could lead to the formation of an intermediate similar to that obtained in the traditional route. Thus, in the present work, we report the use of hydrazides in the synthesis of a substituted phenyl TTT derivative (4-OMe). Various methodological modifications were tested, including different solvents, bases, dehydrating agents, temperatures, and reaction times. The most efficient reaction so far employed three equivalents of 4-methoxybenzohydrazide, one equivalent of cyanuric chloride, six equivalents of pyridine, and an excess of thionyl chloride in acetonitrile, yielding exclusively the tangential TTT isomer in 72% yield after purification by column chromatography. The compound was characterized by its melting point, FTIR and NMR spectroscopy. We are currently broadening the scope of this methodology by employing hydrazides derived from pyridine, acetohydrazide, and hydrazides bearing various substituents (2-OMe, 3-OMe, 4-OMe, 3,4,5-OMe, 4-tert-butyl, 4-NO2, 3-NO2), thereby further validating the efficiency of the methodology. References: [1] R. Huisgen, H. J. Sturm, M. Seidel. Chemische Berichte, 1961, v. 94, n. 6, p. 1555–1562. [2] M. d. S. Kutz, L. A. Suassuna e Bega, C. Francener, G. Farias, F. A. de Campos, H. Bock, I. H. Bechtold, F. Molin, E. Westphal, J. Mol. Struct. 2025, 1321, 139996. [3] H. Detert, Eur. J. Org. Chem. 2018, 2018, 4501-4507. [4] S. Wang, X. Wang, K. H. Lee, S. Liu, J. Y. Lee, W. Zhu, Y. Wang, Dyes Pigm. 2020, 182, 108589. Acknowledgments: UFSC, PPGQ, CAPES, FAPESC and INEO (FAPESP - processo nº 2025/27044-5 e CNPq - processo: 408449/2024-1)

Título do Evento: Workshop do INEO 2026
Cidade do Evento: Nazaré Paulista
Título dos Anais do Evento: Anais do Workshop do INEO 2026
Nome da Editora: Even3
Meio de Divulgação: Meio Digital

Como citar

NUNES, Júlia Goes; OLIVEIRA, Érica Gilioli de; WESTPHAL, Eduard. ACYLHYDRAZIDES AS NEW PRECURSORS FOR THE SYNTHESIS OF TRIS-[1,2,4]TRIAZOLO-[1,3,5]-TRIAZINE CORES.. In: Anais do Workshop do INEO 2026. Anais...Nazaré Paulista(SP) Hotel Estância Atibainha, 2026. Disponível em: https//www.even3.com.br/anais/workshop-do-ineo-2026/1462049-ACYLHYDRAZIDES-AS-NEW-PRECURSORS-FOR-THE-SYNTHESIS-OF-TRIS-124TRIAZOLO-135-TRIAZINE-CORES. Acesso em: 10/08/2026