Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• ]. Acyl or aroyl groups can be introduced into the 4-position of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones via three-component reactions of esters of acylpyruvic acid or of aroylpyruvic acid, respectively, with aromatic aldehydes, and amines. In addition, the resulting 2-pyrrolidinone derivatives also showed

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

• Ekaterina E. Stepanova,
• Maksim V. Dmitriev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

• )-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out. Keywords: acylpyruvic acid

• more electrophilic ketone carbonyls of compounds IV firstly. To overcome these issues, we examined the reaction of acylpyruvic acid (2a) with o-aminothiophenol (1a) in the presence of carbodiimides in various solvents (Table 1). Fortunately, in many cases we succeeded to detect the desired BTA 3a by

• only in trace amounts. This phenomenon can be explained by the formation of intermediates highly sensitive to amines. We believe that the reaction of acylpyruvic acid 2a with o-aminothiophenol (1a) in the presence of carbodiimides proceeded through the formation of 5-phenylfuran-2,3-dione (5a, CCDC