An unprecedented domino radical cyclisation-Smiles rearrangement process affording 3-(2'-aryl-N-methyl acetamido)indolin-2-ones is presented. Experimental rationalisation of this approach and description of an unexpected tricyclic core are also handled.

The ring-opening of 3-aminocyclobutanone oximes enables easy generation primary alkyl radicals, capable undergoing an unprecedented strain-release, desulfonylative radical Truce–Smiles rearrangement, providing divergent access to valuable 1,3 diamines and unnatural ?-amino acids. Characterized by mild conditions wide scope migrating species, this protocol allows the modular assembly sp3-aryls u...

A new synthesis of 4-halo-1H-indoles has been developed from easily available 2,3-dihalophenol derivatives. The key steps are Smiles rearrangement and a one-pot or stepwise Sonogashira coupling/NaOH-mediated cyclization. Subsequent functionalization allows access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles.

Treatment of (ortho-trimethysilyl)aryl phenylsulfonates with a soluble fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls. This new carbon-carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility.

10H-phenothiazines are prepared by Smiles rearrangement. These prepared phenothiazines are used as base to prepare ribofuranosides by treatment with β-Dribofuranosyl-1-acetate-2,3,5-tribenzoate. 10H-Phenothiazines on refluxing with hydrogen peroxide in glacial acetic acid gave 10H-phenothiazine-5,5-dioxides. Their antioxidant and antimicrobial activity have been carried out. The structure of th...

hemistry 2017 been widely used to construct important families of target molecules, aryl ethers, suldes and sulfoxides. Traditionally, these reactions are carried out in organic solvents (e.g., THF, CH3CN, DMSO, and DMF), which may cause potential health, safety, and waste disposal issues. Therefore, transition-metalfree C–O and C–S coupling reactions under greener conditions are desirable, es...