| Synthesis of novel quinazoline-dione derivatives containing 4-(triaryl imidazolyl)phenyl substituent and investigation of their emission behaviors |
| کد مقاله : 1110-ICOC |
| نویسندگان |
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سما طالبی بهنق *، زرین قاسمی دانشگاه تبریز - دانشکده شیمی |
| چکیده مقاله |
| Quinazolin-2,4(1H,3H)-diones are among the most significant and distinctive nitrogen-containing heterocycles. They have attracted increasing attention in synthetic and pharmacological investigations owing to diverse biological activities [1]. This scaffold is present in the structures of pharmacophores and bioactive compounds such as elinogrel [2] and belaperidone [3]. Many therapeutic activities of quinazoline-dione derivatives have been reported, including vasculature-modulating and antiangiogenic activities [4]. Our investigation began with a known tetra-component synthesis of 4-(triarylimidazolyl)aniline derivatives. In the next step, the amino group of these derivatives was converted to the corresponding 2-iodobenzamides via reaction with 2-iodobenzoyl chloride. These benzamide derivatives were then subjected to a thermal reaction with potassium cyanate in the presence of copper(I) iodide as a catalyst, 8-hydroxyquinoline as a ligand, and dimethyl sulfoxide as the solvent (Scheme 1). This process enabled the substitution of the iodine atom at the 2-position of the benzamide with a cyanate ion. Subsequently, an intramolecular cyclization involving the amide NH group occurred, leading to the formation of quinazoline-2,4(1H,3H)-dione derivatives in good yields (59–86%). All the products were characterized by spectroscopic data (FT-IR, ¹H NMR, and ¹³C NMR), and their optical properties were studied using UV–vis and fluorescence spectra (in ethanol solutions, 10⁻⁵ M), and their quantum yields were determined. |
| کلیدواژه ها |
| Tetraarylimidazols, Quinazoline-dione, Ullmann type reaction |
| وضعیت: پذیرفته شده |