Development of methodologies for the regioselective synthesis of four series of regioisomer isoxazoles from β-enamino diketones

Raí G M Silva; Michael J V da Silva; Andrey P Jacomini; Sidnei Moura; Davi F Back; Ernani A Basso; Fernanda A Rosa

doi:10.1039/c7ra13343j

Development of methodologies for the regioselective synthesis of four series of regioisomer isoxazoles from β-enamino diketones

RSC Adv. 2018 Jan 25;8(9):4773-4778. doi: 10.1039/c7ra13343j. eCollection 2018 Jan 24.

Authors

Raí G M Silva¹, Michael J V da Silva¹, Andrey P Jacomini¹, Sidnei Moura², Davi F Back³, Ernani A Basso¹, Fernanda A Rosa¹

Affiliations

¹ Departamento de Química, Universidade Estadual de Maringá (UEM) 87030-900 Maringá PR Brazil farosa@uem.br.
² Laboratório de Produtos Naturais e Sintéticos, Instituto de Biotecnologia, Universidade de Caxias do Sul (UCS) 95070-560 Caxias do Sul RS Brazil.
³ Departamento de Química, Universidade Federal de Santa Maria (UFSM) 97110-970 Santa Maria RS Brazil.

Abstract

Four methodologies are reported for the regioselective synthesis of four series of regioisomer isoxazoles from cyclocondensation of β-enamino diketones and hydroxylamine hydrochloride. Regiochemical control was achieved by varying reaction conditions and substrate structure. The mild reaction conditions used to access 4,5-disubstituted, 3,4-disubtituted, and 3,4,5-trisubstituted regioisomer isoxazoles, as well as the pharmacological and synthetic potential of the products, make these novel methodologies very powerful.