An Efficient Synthesis of Thioesters Starting from N‐Arylthiocarbamates and Indoles: A Newman‐Kwart‐Type Rearrangement

Abstract

An efficient method for synthesizing thioester compounds under metal‐free conditions was reported. Thus, a series of indole‐substituted thioesters were easily obtained in the presence of PhICl2 (dichloroiodo‐benzene) starting from N‐arylthiocarbamates and indoles. This Newman‐Kwart‐type rearrangement reaction features metal free, base free, mild reaction conditions, good functional tolerance, and good yield, showing potential value for preparing some biologically and pharmaceutically active compounds.

I2‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones

“…[12] Later, we also developed an effective method for synthesizing thiocarbamate compounds starting from thioureas and indoles by Newman Kwart type rearrangement. [13] In recent years, enaminones have been widely used as highly reactive intermediate in the synthesis of heterocyclic compounds. In light of the recent advances in organic synthesis starting from enaminone, [14] as well as our long-term interest in organosulfur chemistry to construct various CÀ S and CÀ N bonds, [15] we would like to report an I 2 -promoted [3 + 2] cyclization for the synthesis of polysubstituted thiazol-2(3H)-ones.…”

I2-Cs2CO3 Mediated Intramolecular C2-Amination and Oxidative Rearrangement Cascade of C-3 Phenylthio Indoles: A Route to Synthesize Thiosulfonate-Embedded 2-Iminoindolin-3-ones

“…Organic sulfur compounds and nitrogen-containing heterocycles , are prevalent in natural products, pharmaceuticals, insecticides, and functional materials, making their synthesis a key focus. Thiosulfonates have gained significant prominence recently, finding applications in medicinal chemistry, and materials science.…”