Synthesis of N-Pyrrolyl(furanyl)-Substituted Piperazines, 1,4-Dizepanes, and 1,4-Diazocanes

Mateus Mittersteiner; Valquiria P Andrade; Lucimara L Zachow; Clarissa P Frizzo; Helio G Bonacorso; Marcos A P Martins; Nilo Zanatta

doi:10.1021/acs.joc.9b00867

Synthesis of N-Pyrrolyl(furanyl)-Substituted Piperazines, 1,4-Dizepanes, and 1,4-Diazocanes

J Org Chem. 2019 Jul 19;84(14):8976-8983. doi: 10.1021/acs.joc.9b00867. Epub 2019 Jul 1.

Authors

Mateus Mittersteiner¹, Valquiria P Andrade¹, Lucimara L Zachow¹, Clarissa P Frizzo¹, Helio G Bonacorso¹, Marcos A P Martins¹, Nilo Zanatta¹

Affiliation

¹ Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química , Universidade Federal de Santa Maria , 97105-900 Santa Maria , Rio Grande do Sul , Brazil.

PMID: 31259554
DOI: 10.1021/acs.joc.9b00867

Abstract

The synthetic potential of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one toward the catalyst-free synthesis of N-pyrrolyl(furanyl)-piperazines, 1,4-diazepanes, and 1,4-diazocanes through a telescoped protocol is reported. This three-component one-pot method provided 23 examples with high chemo- and regioselectivity at yields up to 96%.

Publication types

Research Support, Non-U.S. Gov't