Benzyltrimethylammonium Dichloroiodate Catalyzed Four‐Component Synthesis of Fully Functionalized Pyrroles Under Eco‐compatible Conditions

Abstract

Benzyltrimethylammonium dichloroiodate promoted an eco‐compatible synthesis of fully functionalized pyrroles via isocyanide‐based four‐component reactions under solvent‐free conditions that are reported. Benzyltrimethylammonium dichloroiodate supported reaction process including Knoevenagel condensation followed by the Michael type and intramolecular cyclization that gives high yields.

Solvent‐Free Synthesis of Pyrroles: An Overview

“…Pagadala and Kusampally demonstrated the solvent‐free, four‐component synthesis of pyrrole derivatives by using the benzyltrimethylammonium dichloroiodate (BTADCI) catalyst through a highly effective and eco‐friendly strategy [91] . The reaction was found to be completed in 30 to 40 min at 80 °C using 50 mg catalyst.…”

Oxidation of Iodine to Dihaloiodate(I) Salts of Amines With Hydrogen Peroxides and Their Crystal Structures

“…However, this increased reactivity can only be achieved in the presence of superacids ( Filimonov et al, 2008 ). Benzyltrimethylammonium DCI (PhCH 2 Me 3 N + ICl 2 − ) was prepared and used for the iodination of aromatic amines ( Kajigaeshi et al, 1988a ), fenols ( Kajigaeshi et al, 1987 ), aromatic ethers ( Kajigaeshi et al, 1988b ), acetanilides ( Kajigaeshi et al, 1989 ) and even as a catalyst in the four-component synthesis of pyrroles ( Pagadala and Kusampally, 2019 ). Recently, it was also used in the total synthesis of scutellarin ( Liu et al, 2019 ), an enantioselective synthesis of islatravir ( Patel et al, 2020 ) and secalonic acid ( Qin and Porco, 2014 ).…”