Introduction of Ag/CuO/MCM‐48 as an efficient catalyst for the one‐pot synthesis of novel pyran‐pyrrole hybrids

Abstract

Bimetallic silver and copper incorporated mesoporous MCM‐48 (Ag/CuO/MCM‐48) was synthesized by simple wet‐impregnation method. The knowledge about its structural properties was gathered by means of Fourier transform‐infrared, energy‐dispersive X‐ray, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy and Brunauer–Emmett–Teller analyses. The catalytic activity of Ag/CuO/MCM‐48 was examined in the one‐pot three‐component reaction of 3‐(1‐methyl‐1H‐pyrrol‐2‐yl)‐3‐oxopropanenitrile, malononitrile and various aromatic aldehydes leading to novel pyran‐pyrrole hybrid derivatives in reduced reaction times (5–10 min) and excellent yields (88–97%). Application of Ag/CuO/MCM‐48 as a potent heterogeneous catalyst with good reusability up to five times, use of ethanol as an eco‐compatible medium and chromatography‐free work‐up are some crucial green aspects of this procedure.

Ag/CuO/MCM-48 AS A POTENTIAL CATALYST FOR THE SYNTHESIS OF SYMMETRICAL AND UNSYMMETRICAL POLYHYDROQUINOLINES

“…Following our prior efforts to prepare heterogeneous catalysts and apply them for the synthesis of heterocyclic systems [38, 40-42, 44, 45], herein, a facile Hantzsch condensation in the presence of Ag/CuO/MCM-48 as an effective heterogeneous and reusable catalyst in EtOH has been employed to obtain diversely substituted symmetrical and unsymmetrical polyhydroquinoline 4a-f and 5a-f with high to excellent yields (Scheme 1). Ag/CuO/MCM-48 was synthesized by the procedure described in our previous report [42].…”

“…Ag/CuO/MCM-48 was prepared according to our previous report [42]. Arylaldehyde 1 (1 mmol), dimedone 2 (2 mmol), ammonium acetate (1.3 mmol) and Ag/CuO/MCM-48 (30 mg) were taken in 4 mL EtOH in a round-bottomed flask and the reaction mixture was reflux for an appropriate reaction time (Table 2).…”

“…As a continuation of our ongoing endeavors in developing novel and practical multicomponent reactions to synthesize heterocyclic compounds of biological importance [37][38][39][40][41][42][43][44][45], we herein present the catalytic efficiency of Ag/CuO/MCM-48 for the multicomponent synthesis of symmetrical and unsymmetrical polyhydroquinoline derivatives under identical reaction conditions (Scheme 1). Recently, unsymmetrical polyhydroquinoline motifs have been recognized as lead molecules in antidiabetic drug discovery [46].…”

γ‐Fe2O3@HAp@PBABMD@Cu magnetic nanoparticles: Efficient, green, and recyclable novel nanocatalyst for the synthesis of densely functionalized pyrrole‐pyrido[2,3‐d]pyrimidine hybrids

“…Considering the biological importance of pyrrole scaffolds, development of one-pot synthetic routes to construct a heterocyclic system containing this structural motif remains a topic of attention. [36][37][38][39][40][41][42] One of the main principles of green chemistry is to avoid the use or production of dangerous substances in the design, making, and application of the chemical product. On the basis of this fact, designing new methods by employing multi-component reactions (MCR) without using any harmful organic solvents [43][44][45][46] and using heterogeneous, recyclable catalysts makes these reactions powerful green chemical technology procedures, resulting in minimal pollution and waste material.…”

“…Similarly, the pyrrole skeleton, which is one of the most prominent N ‐heterocycles, is the key structure in natural and pharmaceutically substantial molecules and exhibited an extensive range of biological activities (Figure 1d,e). Considering the biological importance of pyrrole scaffolds, development of one‐pot synthetic routes to construct a heterocyclic system containing this structural motif remains a topic of attention 36–42 . One of the main principles of green chemistry is to avoid the use or production of dangerous substances in the design, making, and application of the chemical product.…”