MPC@But-SO3H a mesoporous heterogeneous organocatalyst in one-pot tandem synthesis of dihydroindeno[1,2-b]pyrrole derivatives

Abstract

A sustainable, metal-free, and highly efficient protocol for the synthesis of dihydroindeno[1,2-b]pyrrole derivatives via a tandem one-pot three-component reaction in aqueous medium at room temperature using an effective and reusable mesoporous heterogeneous organocatalyst, MPC@But-SO3H has been developed. MPC@But-SO3H was easily synthesized using a melamine-based covalent organic polymer and 1,4-butane sultone. The organocatalyst was well characterized by numerous spectroscopic techniques such as Fourier Transform Infrared (FTIR), Brunauer-Emmett-Teller (BET), X-ray photoelectron spectroscopy (XPS), Powder X-ray diffraction (PXRD), Scanning Electron Microscope (SEM), Energy Dispersive X-ray (EDX), elemental mapping, and Thermal Gravimetric (TG) analyses. The catalyst displayed excellent catalytic potential, high thermochemical stability, and reusability for up to eight catalytic cycles. It offered the title compounds in excellent yields (˃90%) in a short reaction time (9-14 min). The synthesized compounds were characterized through FTIR, 1H, and 13C Nuclear Magnetic Resonance (NMR), and the molecular structure of 2-(benzylamino)-3a,8b-dihydroxy-1-methyl-3-nitro-3a,8b-dihydroindeno[1,2-b]pyrrol-4(1H)-one (4a) was confirmed by the Single Crystal XRD (SC-XRD) analysis. The key features of the present protocol include the use of water as a green solvent, zero involvement of any metal, sustainable reaction conditions, easy catalyst recovery, and a simple work-up procedure. The calculations for green metrics parameters further supported the greenness and sustainability of the protocol.