Iodo-sulphonylation of 1,6-enynones: a metal-free strategy to synthesizeN-substituted succinimides

Abstract

An iodine-mediated radical cyclization of 1,6-enynones with sulfonyl hydrazides using tert-butyl hydroperoxide (TBHP) as an oxidant has been developed for the synthesis of iodo-sulfonylated-succinimide derivatives. The notable advantages of the...

An investigation of the biological applications of sulphonated succinimides: in vivo toxicity to zebrafish larvae as well as antioxidant and antimicrobial potential

“…The NMR, HR-MS data of all the compounds and the single-crystal XRD of compound 4aa are already reported in our previous work. 35 In this work, we studied the biological activities of both electron-donating and withdrawing groups of the succinimide compounds 4aa–4la , 4ba–ha , and 4ia–4ma . In order to explore the impact of the iodide functionality, we modified/expanded the chemical space to get new derivatives.…”

“…34 Based on the above reports and the biological importance of the succinimide moiety and sulphonyl scaffolds, significant interest has arisen in designing hybrid compounds of succinimide with sulphonyls to explore their biological activities. Compounds (4aa-4la, 4ba-4ma, 6, and 7) were synthesized in our previous work 35 and their methodology was developed already. Further, we wanted to explore the biological importance of these sulphonated succinimide compounds.…”

“…Further, we wanted to explore the biological importance of these sulphonated succinimide compounds. In this investigation, the toxicity of the sulphonated succinimides obtained from our previous work 35 toward zebrafish embryos was studied. Additionally, their radical-scavenging effect was analyzed using DPPH and ABTS.…”

Applications of sulfonyl hydrazides in radical cyclization of alkenes

“…Recently, Ramasamy, Senadi and co-workers developed an I 2 /TBHP-promoted radical cascade cyclization of 1,6-enynones to afford iodo-sulfonylated succinimide derivatives through the formation of C–S, C–C, and C–I bonds (Scheme 7-6). 28 Metal-free conditions, broad functional group tolerance, column chromatography-free purification, high stereoselectivity ( E isomer), and the cascade construction of three new bonds (C–S, C–I, and C–C) were the main advantages of the developed method.…”

Visible-Light-Initiated Catalyst-Free Radical Annulation Reactions of 1,6-Enynes and Aryl Sulfonyl Bromide to Assemble Sulfonation/Bromination Succinimide Derivatives

“…If more atoms or groups can be inserted into the product structures of the 1, n -enyne radical cyclization reactions, such reactions have the high atomic economy. Although many polyfunctionalization reactions of 1, n -enynes have been reported, they usually required the use of different metal catalysts or additives, which reduces the effectiveness and practical value of the reactions …”