Design and synthesis of PDSPTCF as an influential Brønsted-Lewis acidic catalyst for the producing benzo[a]benzo[6,7]chromeno[2,3-c]phenazines

Abstract

Abstract Initially, 4,4'-(1,4-phenylene)di(sulfonic)pyridinium tetrachloroferrate (PDSPTCF) as a novel organic–inorganic hybrid salt was synthesized and identified by elemental mapping, energy-dispersive X-ray spectroscopy, inductively coupled plasma atomic emission spectrometer, Raman spectroscopy, Fourier-transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, vibrating-sample magnetometry, and thermal gravimetric (TG) techniques. Then, the catalytic performance of this hybrid salt was assessed for the producing benzo[a]benzo[6,7]chromeno[2,3-c]phenazine derivatives via one-pot multicomponent domino reaction (MDR) of benzene-1,2-diamine, 2-hydroxynaphthalene-1,4-dione and aldehydes under optimal conditions (70 °C, solvent-free, 5 mol% PDSPTCF) in short reaction times and high yields. Highly efficacy of the PDSPTCF for the production of benzo[a]pyrano[2,3-c]phenazines can be assigned to the synergistic effect of Lewis and Brønsted acids, and having two positions of each acid (i.e., FeCl4ˉ and –SO3H). In addition, this catalyst showed good reproducibility with six cycles of recycling.

Keywords

• Benzo[a]benzo[6,7]chromeno[2,3-c]phenazine
• Multicomponent domino reactions (MDRs)
• 4,4'-(1,4-phenylene)di(sulfonic)pyridinium tetrachloroferrate (PDSPTCF)
• Brønsted-Lewis acidic catalyst
• Organic–inorganic hybrid salt