I-CsCO Mediated Intramolecular C2-Amination and Oxidative Rearrangement Cascade of C-3 Phenylthio Indoles: A Route to Synthesize Thiosulfonate-Embedded 2-Iminoindolin-3-ones.

An efficient, transition-metal-free protocol employing I/CsCO for the synthesis of thiosulfonate containing 2-iminoindolin-3-ones motifs has been developed from C-3 phenylthio indoles. The reaction proceeded through intramolecular cyclization involving C-N bond formation, leading to the formation of indole-fused benzothiazines as a key intermediate. Remarkably, CsCO played a crucial role in the reaction as an oxygen source, enabling oxidative rearrangement with [1,4]-sulfonyl migration to furnish the final products with the formation of multiple functional groups such as C═O, C═N, and S-SO.

Iodine-Catalyzed Synthesis of Benzo-β-carbolines through Desulfurative Cyclization of 2-(1-Indol-3-ylsulfanyl)-phenylamines with Aryl Methyl Ketones.

A novel transition metal-free strategy for the synthesis of benzene-fused β-carboline scaffolds has been developed. This protocol offers a rapid and direct pathway to access the benzene fused β-carboline from 2-(1-indol-3-ylsulfanyl)-phenylamines and aryl methyl ketones using an efficient catalytic system of I/DMSO. The present mild protocol proceeds through the sequential reactions of Kornblum oxidation, Pictet-Spengler cyclization, and desulfurization to afford the desired products in excellent yields up to 99%.