Synthesis of Succinimides via Intramolecular Alder-Ene Reaction of 1,6-Enynes

Abstract

A novel and convenient method has been developed for the facile synthesis of functionalized succinimide derivatives via intramolecular Alder-ene reaction of 1,6-enynes. This reaction features mild and metal-free reaction conditions, which offers a green and efficient entry to synthetically important succinimide scaffolds. Preliminary mechanistic studies suggest that a diradical intermediate might be involved in this transformation.

Antioxidant Molecules Isolated from Edible Prostrate Knotweed: Rational Derivatization to Produce More Potent Molecules

“…Similarly, the succinimide is a known class of drugs for neuropharmacology and inflammation [44]. Various derivatives of succinimide-type compounds can be synthesized with different methods [51][52][53][54]. In our research, we noticed that compounds 2, 4, and 5 are potent antioxidant Oxidative Medicine and Cellular Longevity molecules.…”

Time and Atom Economical Regio‐ and Chemoselective Radical Cyclization of Unactivated 1,6‐Enynes Under Metal‐ and Oxidant‐Free Conditions

“…Based on the above mentioned mechanistic results and previous reports [2–7,9–11,14−16] we propose a plausible reaction mechanism as depicted in Scheme 6. Under blue LED light compound 4‐methylbenzenesulfonyliodide ( 2 a ) absorb the light, simultaneously produces sulfone ( 2 a′ ) and iodine ( 2 a’′ ) radicals via homolytic bond fission [10] .…”

“…Finally, the vinyl radical intermediate trap the available iodine radical in a less steric site [16] to deliver the final product (Z)-4-(iodo(phenyl)methylene)-3-phenyl-1-tosyl-3(tosylmethyl)pyrrolidine (4 aa). [14]…”

“…The stable radical via 5‐ exo ‐dig cyclization with alkyne in 1,6‐enyne produce the vinyl radical intermediate ( B ). Finally, the vinyl radical intermediate trap the available iodine radical in a less steric site [16] to deliver the final product ( Z) ‐4‐(iodo(phenyl)methylene)‐3‐phenyl‐1‐tosyl‐3(tosylmethyl)pyrrolidine ( 4 aa ) [14] …”

Divergent construction of 3-(indol-2-yl)succinimide/maleimide and fused benzodiazepine skeletons from 2-(1H-indol-1-yl)anilines and maleimides

“…1). 1 In addition, it is a versatile building block frequently used for the preparation of pyrrolidine, pyrazole, carboxylic acid, ester, diamide, maleimide, γ-lactam, etc . On the other hand, indole constitutes the key structural scaffold of numerous medicines, pesticides, dyes and pigments.…”