One‐pot Synthesis, Crystal structure, and Bioactivity of N‐Phenoxyacetyl‐2,4,5‐trisubstituted‐1,3‐oxazolidines

Abstract

N‐phenoxyacetyl‐1,3‐oxazolidine derivatives were synthesized by the cyclization and acylation with β‐amino alcohol, ketone, and phenoxyacetyl chloride as the starting materials. All compounds were characterized by IR, 1H NMR, 13C NMR, ESI‐MS, and elemental analysis. The configuration of 4a was determined by X‐ray crystallography. The preliminary biological tests showed that all products could protect soybean against injury caused by 2,4‐D butylate to some extent.

Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side‐Chain in 2‐Nitroimidazoles

“…Within the oxazolidine ring, C6 and O1 deviate the most (−0.160 and 0.156 Å, respectively) from the mean plane, although the N‐atom on this ring is disordered and, within the minor fragment, C6 and N3A deviate from the mean plane by 0.249 and −0.215 Å, respectively. X‐ray data in recent papers on substituted oxazolidines that do have biological properties have noted planar , twisted , and envelope‐type rings. The synthetic methodology in these and other oxazolidine systems varies considerably , the closest to formation of 3 being one reported by Ye's group ; Scheme shows both reactions that involve incorporation of a carbonyl oxygen and an amine nitrogen into the oxazolidine ring, although the process for 3 is intramolecular, whereas the other is intermolecular.…”

“…X‐ray data in recent papers on substituted oxazolidines that do have biological properties have noted planar , twisted , and envelope‐type rings. The synthetic methodology in these and other oxazolidine systems varies considerably , the closest to formation of 3 being one reported by Ye's group ; Scheme shows both reactions that involve incorporation of a carbonyl oxygen and an amine nitrogen into the oxazolidine ring, although the process for 3 is intramolecular, whereas the other is intermolecular. Such an intramolecular cyclization within a triflate derivative of Etanidazole has been suggested previously , but no evidence was presented in either report.…”

Protective efficacy of phenoxyacetyl oxazolidine derivatives as safeners against nicosulfuron toxicity in maize

“…In a previous study, this new series of compounds was tested for the protective effect of phenoxyacetic acid herbicides. 36 In order to expand the application of these compounds, SU safety experiments were carried out in the present study. Nicosulfuron was selected as a representative SU to study the detoxification of safeners.…”

Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

“…Two compounds based on acylsulfamoylbenzamide have better bioactivities than cyprosulfamide and could serve as leading compounds in the design of new safeners. In addition, isoxadifen-ethyl was designed by combining the active substructures of known active molecules [ 13 ]. Furthermore, molecular docking has been performed to compare the binding affinities of herbicides and the target compound with the target enzyme (i.e., ALS) [ 14 ].…”

“…However, these reactions, which involve cyclization and acylation, are time-consuming and complicated. According to our previous research [ 13 ], the final products were directly synthesized by a one-pot reaction ( Scheme 3 ), representing an efficient and time saving route. The aim of this study was to synthesize new methyl ( R )- N -benzoyl/dichloroacetyl-thiazolidine-4-carboxylates and determine their biological activities using biological tests.…”