Synthesis and Identification of Some New tetrazolin-1-yl, Imidazolidine-4-one, and Thiazolidine-4-one Derivatives from pyromellitic diimide and Their Antioxidant Activities Investigation

Abstract

 This work includes the synthesis of a new five-membrane heterocyclic ring of zolidines derivatives. These derivatives of compounds were synthesized by reaction of pyromellitic diimide was solved in dry DMF with sodium hydrate to produce salt pyromellitic diimide right after that add ethyl chloro acetate to give N, N´-bis (ethyl acetate) Pyromellitic diimide this product is the first compound (1) then with excess hydrazine hydrate in absolute ethanol to obtain hydrazaide derivatives compounds (2). After that compound (2) reacts with p-substituted aromatic aldehydes to give Schiff base compounds (3-7). The Schiff base compounds exhibit versatile reactivity, leading to the formation of various heterocyclic derivatives. When reacted with sodium azide, they produce tetrazolidine derivatives (8-12). Similarly, their reaction with 2-amino acetic acid yields imidazolidin-4-one derivatives (13-17), while treatment with 2-mercapto acetic acid results in the formation of thiazolidin-4-one derivatives (18-22). These transformations highlight the adaptability of Schiff base compounds in synthesizing a wide range of structurally diverse and functionally significant heterocyclic compounds. The produced compounds' physicochemical characteristics and melting points were identified. To identify novel compounds, spectral approaches such as ¹H-NMR, ¹³C-NMR, and FT-IR were employed. Assessments from both computational and experimental methods confirm the promising bioactivity of the produced zolidines derivatives as antioxidants.