Synthesis of Novel 2-Aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones Via Ultrasound Irradiation

Author(s)

Daniela P. Gouvêa ^[1] ; Gabriele A. Berwaldt ^[2] ; Patrícia D. Neuenfeldt ^[3] ; Ricardo J. Nunes ^[4] ; Wanda P. Almeida ^[5] ; Wilson Cunico ^[6]

Affiliation

^[1] Universidade Federal de Pelotas. Laboratório de Química Aplicada a Bioativos - Brasil

^[2] Universidade Federal de Pelotas. Laboratório de Química Aplicada a Bioativos - Brasil

^[3] Universidade Federal de Santa Catarina. Laboratório Estrutura e Atividade - Brasil

^[4] Universidade Federal de Santa Catarina. Laboratório Estrutura e Atividade - Brasil

^[5] Universidade Estadual de Campinas. Laboratório de Desenvolvimento de Fármacos e Medicamentos - Brasil

^[6] Universidade Federal de Pelotas. Laboratório de Química Aplicada a Bioativos - Brasil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 27, n. 6, p. 1109-1115, 2016-06-00.

Abstract

This study describes the synthesis of fourteen thiazinanones from a multicomponent reaction of 2-morpholinoehtylamine (as primary amine), arenealdehydes (as carbonyl compound) and the mercaptopropionic acid using both conventional (thermal heating) and ultrasound methodologies. Through thermal heating methodology, the thiazinanones were obtained in 49 to 97% yields for 16 hours and through sonochemistry methodology, the reaction time was reduced for 25 minutes with yields 41 to 88%. The full identification and characterization of unpublished heterocycles were achieved by proton (1H) and carbon 13 (13C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry and infrared. Some of them were also characterized by elemental analysis. (AU)

• FAPESP's process: 13/18203-5 - Synthesis of molecular hybrids derived from 4-quinolones as potential drug candidates to treat Alzheimer's Disease
• Grantee: Wanda Pereira Almeida
• Support Opportunities: Regular Research Grants