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

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 The full identification and characterization of unpublished heterocycles were achieved by proton ( 1 H) and carbon 13 ( 13 C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry and infrared. Some of them were also characterized by elemental analysis.

Chemistry of Substituted Thiazinanes and Their Derivatives

“…The products were formed via the intermediates 75a-n [44] Thiazinanones 76a-n were synthesized via three-component reactions between aldehydes, 2-morpholinoethanamine (74) and 3-mercaptopropionic acid under both thermal and ultrasonication conditions. The products were formed via the intermediates 75a-n [44] (Scheme 19). Thiazinanones 76a-n were synthesized via three-component reactions between aldehydes, 2-morpholinoethanamine (74) and 3-mercaptopropionic acid under both thermal and ultrasonication conditions.…”

“…Thiazinanones 76a-n were synthesized via three-component reactions between aldehydes, 2-morpholinoethanamine (74) and 3-mercaptopropionic acid under both thermal and ultrasonication conditions. The products were formed via the intermediates 75a-n [44] (Scheme 19). 4-Oxo-1,3-thiazinan-11-oxoundecensulfanyl propanoic acid 134 was prepared in two steps: The hydrazine (N'-(3-nitrobenzylidene)undec-10-enehydrazide) (132) was first prepared by refluxing 10-undecenoic acid hydrazide 131 with m-nitrobenzaldehyde in anhydrous benzene.…”

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

“…vs. 19 h). 137 Another group found optimal conditions for their reaction when a polyethylene glycol (PEG)-OSO 3 H catalyst was used in combination with ultrasound in water (Scheme 61). PEG-OSO 3 H acted as both an acid catalyst and a phase transfer catalyst.…”

Mechanochemical and sonochemical heterocyclizations

“…This approach has also been widely exploited in medicinal chemistry to provide libraries of biologically active compounds, including heterocycles. Gouvêa et al 34 have reported the US-assisted synthesis of thiazinan-4-one derivatives 26 via the MCR of 2-morpholinoehtylamine, aromatic aldehydes, and 3-mercaptopropionic acid (Scheme 21). The thiazinanones were obtained in 41-88% yield in only 25 min using a US probe (20 kHz).…”