Enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives by Fe₃O₄@PS‐arginine as an efficient chiral magnetic nanocatalyst

Abstract

A novel chiral magnetic nanocatalyst was prepared by the surface modification of Fe3O4 magnetic nanoparticles (MNPs) with a chloropropylsilane and further by arginine to form Fe3O4@propylsilan‐arginine (Fe3O4@PS‐Arg). After the structural confirmation of Fe3O4@PS‐Arg synthesized MNPs by Fourier transform‐infrared, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy, vibrating‐sample magnetometry and thermogravimetric analyses, their catalytic activity was evaluated for one‐pot enantioselective synthesis of 3‐amino‐1‐aryl‐1H‐benzo[f]chromene‐2‐carbonitrile derivatives. The results showed that in the presence of 0.07 g Fe3O4@PS‐Arg nanocatalyst and ethanol as solvent, the best reaction yield (96%) was obtained in the least time (5 min). Easy operation, reusability and stability, short reaction time, high reaction yields and good enantioselectivity are the major advantages of the newly synthesized nanocatalyst. Also, this study provides a novel strategy for further research and investigation on the synthesis of new reusable enantioselective catalysts and chiral compounds.

Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe3O4@PS‐Arginine[HSO4] as an efficient magnetic nanocatalyst

“…Fe 3 O 4 and Fe 3 O 4 @PS-Arg MNPs were synthesized according to our previous reports. [40,41] (1 mmol) and Fe 3 O 4 @PS-Arg[HSO 4 ] MNPs (0.07 g) in 5 mL ethanol was refluxed. After completion of the reaction (monitored by TLC), 5 mL ethanol was added and the precipitate was dissolved at the hot ethanol.…”

“…The structure of these nanoparticles was confirmed by FT-IR spectroscopy ( Figure 1A-c). [40] We studied synthesis of 2-amino-4-(4-nitrophenyl) benzo[h]quinoline-3-carbonitrile (5a) by the reaction of α-naphthilamine (1 mmol), malononitrile (1 mmol) and 4-nitrobenzaldehyde (1 mmol) as a model reaction in absence and presence of Fe 3 O 4 @PS-Arg as catalyst (Scheme 2). As the results are shown in Table 1, no product was obtained, even with prolonged reaction times (60 minutes) and with increasing reaction temperature to 110 C (Table 1, entry 1-3).…”

“…[35] In our recently studies, we designed highly efficient magnetic nanocatalysts for the synthesis of heterocyclic compounds by functionalizing Fe 3 O 4 MNPs with amino acids. [36][37][38][39][40] One of these nanocatalysts is Fe 3 O 4 @ Propylsilan-Argenine (Fe 3 O 4 @PS-Arg), which was firstly synthesized by us as a chiral catalyst and used for the enantioselective synthesis of chromene derivatives. [40] In this study, we wish to investigate the efficacy of Fe 3 O 4 @PS-Arg[HSO 4 ] as a novel catalyst for the synthesis of some acridine and novel quinoline derivatives.…”

“…[36][37][38][39][40] One of these nanocatalysts is Fe 3 O 4 @ Propylsilan-Argenine (Fe 3 O 4 @PS-Arg), which was firstly synthesized by us as a chiral catalyst and used for the enantioselective synthesis of chromene derivatives. [40] In this study, we wish to investigate the efficacy of Fe 3 O 4 @PS-Arg[HSO 4 ] as a novel catalyst for the synthesis of some acridine and novel quinoline derivatives. Successful synthesis of two important families of heterocycles (quinoline and acridin) with a high yield and in a minimum of reaction time shows that, this catalyst can be effectively used for the synthesis of other heterocyclic families.…”

“…In our recently studies, we designed highly efficient magnetic nanocatalysts for the synthesis of heterocyclic compounds by functionalizing Fe 3 O 4 MNPs with amino acids [36–40] . One of these nanocatalysts is Fe 3 O 4 @Propylsilan‐Argenine (Fe 3 O 4 @PS‐Arg), which was firstly synthesized by us as a chiral catalyst and used for the enantioselective synthesis of chromene derivatives [40] .…”