Proposal for an ecofriendly and economic strategy for efficient radioiodination of coumarin derivatives

• Published in: Applied radiation and isotopes Vol. 151; pp. 265 - 273
• Main Authors: Khatir–Hamdi, Nejla, Makhloufi-Chebli, Malika, Silva, Artur M.S., Brahimi, Méziane, Grib, Hocine
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.09.2019
• Subjects: Chromatography, High Pressure Liquid; Cold-iodination; Costs and Cost Analysis; Coumarin; Coumarins - chemistry; Cyclization; Ecofriendly strategy; Electrophilic substitution; Iodine Radioisotopes - chemistry; Radioiodination; Spectrophotometry, Ultraviolet; Theoretical calculation; Ecofriendly strategy; Radioiodination; Theoretical calculation; Electrophilic substitution; Cold-iodination; Coumarin
• ISSN: 0969-8043; 1872-9800
• DOI: 10.1016/j.apradiso.2019.06.024

Combination of the calculation of reactivity descriptors and the cold iodine test for some coumarin derivatives was used in order to optimize the radioiodination reaction. The strongly nucleophilic predicted coumarins were subjected to the action of cold iodine. With two coumarins substituted at 3 by the 2-hydroxybenzoyl group, iodination did not occur but a product of intramolecular heterocyclization was obtained. This strategy is useful for economic and environmentally friendly radioiodination. Combination of the calculation of reactivity descriptors and the cold iodine test for some coumarin derivatives in order to optimize the radioiodination reaction. The strongly nucleophilic predicted coumarins were subjected to the action of cold iodine. With two coumarins substituted at 3 by the 2-hydroxybenzoyl group, iodination did not occur but a product of intramolecular heterocyclization was obtained. This strategy is useful for economic and environmentally friendly radioiodination. [Display omitted] •The calculation of global and local nucleophilicity parameters for coumarin derivatives.•Iodination tests with cold iodine and analysis of the compounds obtained.•The iodonium cation causes intramolecular heterocyclization without iodination.•The combination of theoretical calculations - cold iodine is a useful strategy.