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Divergent Regioselective Synthesis of Functionalized 1,2,3-1H-Triazoles from Nitriles and Arylazides under Metal- and/or Solvent-free Conditions.
Petzold Pauli, Fernanda; de Oliveira Lima Filho, Edson; de Almeida Ribeiro Oliveira, Gerlon; Morais Lião, Luciano; Rangel Campos, Vinicius; da Silva Magalhães Forezi, Luana; Francisco Ferreira, Vitor; de Carvalho da Silva, Fernando.
Afiliação
  • Petzold Pauli F; Universidade do Estado do Rio de Janeiro, Química Orgânica, BRAZIL.
  • de Oliveira Lima Filho E; Universidade Federal Fluminense, Química Orgânica, BRAZIL.
  • de Almeida Ribeiro Oliveira G; Universidade Federal de Goiás, Química, BRAZIL.
  • Morais Lião L; Universidade Federal de Goiás, Química, BRAZIL.
  • Rangel Campos V; Universidade Federal Fluminense, Química Orgânica, BRAZIL.
  • da Silva Magalhães Forezi L; Universidade Federal Fluminense, Química Orgânica, BRAZIL.
  • Francisco Ferreira V; Universidade Federal Fluminense, Tecnologia Farmacêutica, BRAZIL.
  • de Carvalho da Silva F; Universidade Federal Fluminense, Organic Chemistry, Outeiro de São João Batista s/n, 24020141, Niteroi, BRAZIL.
Chem Asian J ; : e202400845, 2024 Oct 01.
Article em En | MEDLINE | ID: mdl-39352621
ABSTRACT
Highly selective and divergent syntheses, which are crucial in both organic synthesis and medicinal chemistry, involve significant advancements in compound accessibility. By modifying α-cyano esters into α-cyano ketones, the synthesis pathway broadens to include a diverse range of 4-CN, 5-amino, and 5-arylamino derivatives of 1,2,3-triazoles, which are achieved notably through the Dimroth rearrangement. This versatility extends further with the potential for a triple cascade reaction, leading to the production of carboximidamide compounds, which are facilitated by the Cornforth rearrangement. Advancements in compound accessibility not only expand the repertoire of synthesized molecules but also open new avenues for potential pharmacological agents. Building on these findings, we have developed an innovative and efficient method for the divergent synthesis of functionalized 1,2,3-triazoles. This method strategically utilizes α-cyanocarbonyls and arylazides by harnessing their reactivity and compatibility to orchestrate a variety of molecular transformations. By optimizing these substrates, our goal is to simplify synthetic routes, improve product yields, and accelerate the discovery and development of new chemical entities with promising biological activities.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chem Asian J Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chem Asian J Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha