Recent Developments in Nanocatalyzed Green Synthetic Protocols of Biologically Potent Diverse O-Heterocycles—A Review
Abstract
:1. Introduction
2. Nanocatalyzed Green Synthesis of Various O-Heterocycles
2.1. Synthesis of Furans
- Khodaei et al. developed 4-carboxybenzyl sulfamic acid functionalized Fe3O4 NPs as a new magnetic five-fold recyclable NC for the rapid one-pot production of furan-2(5H)-ones [57] (Scheme 5a). According to substrate scope data, the proposed MNC displayed outstanding bearing strength against diverse substituents on aldehydes or anilines. According to the postulated mechanism, the acetylic carbonyl was protonated and then attacked by aniline to generate an enamine (I). The protonated aldehyde then interacted with the created enamine, forming an intermediate (II) by rearrangement. After dehydration, the carbonyl group of this newly created intermediate (III) was protonated to cyclized, yielding the desired product (Scheme 5b).
- Shirzaei et al. developed a silica-coated magnetic iron NC doped with thiocarbohydrazide for the quick production of furan derivatives [58] (Scheme 5a). According to a substrate scope investigation, the type of substituents affects the product yield and reaction speed. According to the findings, aromatic aldehydes containing ERG (electron-releasing groups) produced better yields in less time than EWGs (electron-withdrawing groups). The mechanistic research showed that an intermediate (I) was formed via the condensation of aniline and acetylene, which then condensed with activated aldehydes to produce a new intermediate (II). The required derivative of furan was obtained via an intramolecular Michael addition and proton removal of this newly formed intermediate (III) (Scheme 5c). The five-time reusability and high degree of activity make the proposed NC superior to other nonmagnetic catalysts.
- Using sulfamic-acid-2-Aminobenzothiazole-6-carboxylic-acid-adorned Fe3O4 NPs, Hao et al. created a novel organic–inorganic hybrid NC (SA-ABTCA-Fe3O4) that allowed for effective production of 3,4,5-trisubstituted furan-2(5H)-ones [59] (Scheme 5a). The NC was four times recoverable and showed good tolerance for the substituent pattern. According to mechanistic results, 4-aminopyridine and DMAD first created an enamine (I), which then interacted with protonated benzaldehyde to form an intermediate (II). The produced intermediate was subsequently cyclized after undergoing a proton exchange to provide the required product (Scheme 5d). This green NC demonstrated strong reversibility and allowed for a clean operation in a short amount of time, making the protocol more practical and cost-effective.
2.2. Synthesis of Chalcones—The Heterocyclic Intermediate
- Aryan et al. created a series of unique nanocomposites by employing manganese ferrite (MnFe2O4 NPs) catalyst to modify the surface of natural clinoptilolite [67]. In the aldol-type Claisen–Schmidt process to produce chalcones (Scheme 8a), one of the nanocatalysts demonstrated strong catalytic performance. The proposed synthesis was made faster and more efficient due to robust catalytic synergy between MnFe2O4 NPs and the natural clinoptlolite interface. The substrate scope revealed that the suggested NC was highly tolerant of reactant substituents. According to the mechanistic proof, the acetophenone and benzaldehyde were activated by the nanocatalyst’s dual Lewis acidic and Bronsted basic features. The presence of O2− in the NC made the enolate formed from acetophenone more nucleophilic, which initiated the attack on benzaldehyde, resulting in the formation of an intermediate (I) that, following dehydration, supplied the desired product (Scheme 8b). The NC was readily filtered out of the reaction mixture and reused up to four times without losing any catalytic performance.
- Borade and his colleagues employed a sol-gel autoignition approach to produce the zinc ferrite (ZnFe2O4 NPs) which they used as a green fuel and as an efficient NC for manufacturing chalcones (Scheme 8a) [68]. The proposed nanocatalyst’s Lewis acidic site aided in the enolization of aryl ketone and activated the benzaldehyde carbonyl group for nucleophilic attack (Scheme 8c). Overall, the proposed approach was shown to be efficient due to its effective MW assistance, solvent-free condition, eco-friendliness, shortened reaction time, fast recovery, and continuous five-cycle reuse of NC.
2.3. Synthesis of Coumarins
- Mirosanloo et al. fabricated a novel biosupported (CNC-AMPD-Pd) NC on palladium NPs utilizing 2-Amino pyrimidine nanocellulose as a support and tested its catalytic performance in Pechmann condensation to generate coumarin derivatives [76] (Scheme 11a). The proposed NC could be easily recycled and reused up to four times without losing any catalytic activity. According to the proposed mechanism, the CNC-AMPD-Pd catalyzed Pechmann condensation generated an olefinic bond by dehydration while concurrently eliminating ethanol to obtain the required coumarin (Scheme 11b). The proposed technique has the advantages of a reusable catalyst, solvent-free environment, no Pd leaching into the reaction solution, faster reaction times, and simple setup.
- Pakdel et al. proposed a six-time-recyclable magnetic-core-shell-like Fe3O4@Boehmite-NH2-CoII NPs for solvent-free Pechmann condensation [77] (Scheme 11a). The reliance of suggested NC on the phenol substitution pattern was revealed by the substrate scope discovery. The results showed that phenols with ERG-generated high yields of the intended product, whereas EWG were found to be less reactive or unreactive, as the presence of ERG was actually responsible for the nucleophilic addition of phenol to the carbonyl group of β-ketoester. Mechanistic findings showed that the β-ketoester was first activated and was then attacked by substituted phenols, resulting in the formation of an intermediate (I). Then, after the rearomatization of (I), a new intermediate (II) was formed, of which simultaneous transesterification and ring closure finally produced coumarin after dehydration (Scheme 11c).
- To enable effective US-assisted coumarin production (Scheme 11a), Zarei et al. produced a new magnetic HFe(SO4)2·4H2O-chitosan nanocomposite [78] (HFe(SO4)2·4H2O-Ch NCs). According to substrate scope data, phenols containing ERG produced coumarin at a faster rate and with a higher yield than phenols containing EWG. Due to steric hindrance and strong electronegativity, EAA reacted faster than ethyl-4-nitroacetoacetate and 4-chloroacetoacetate. The reported catalyst is easily separated by an external magnetic field, and it can be recycled and reused up to seventeen times. These characteristics make the NCs the most efficient catalyst.
- Yuan et al. developed a copper-supported 5-oxo-4,5-dihydropyrrole-3-carboxylic-acid-functionalized Fe3O4 NPs (Cu(II)-OHPC-Fe3O4) as a new magnetic NC for green, solvent-free coumarin synthesis via Pechmann condensation [79] (Scheme 11a). According to the mechanistic findings, the activated EAA first encountered a nucleophilic attack from phenol, forming an intermediate (I) that underwent intramolecular cyclization. After removing the ethanol, the appropriately generated cyclic intermediate (II) yielded the required coumarin (Scheme 11d). The nanocatalyst’s large surface area, chemical stability, four-time recyclability, low leaching into the environment, and superior accessibility make it more appealing.
- For the US-assisted green synthesis of coumarin derivatives [80] (Scheme 11a), Bonab et al. developed a new magnetic core-shell of Fe3O4@c@PeS-SO3H NC. During the investigation of the substrate scope, it was discovered that the type and position of phenol substituents had a significant impact on the catalyst’s performance. In contrast to the EWG, the phenols with ERG promoted synthesis in a shorter reaction time. According to the mechanistic protocol, the carbonyl group of the β-ketoester was first protonated with the proposed NC to render it vulnerable to phenol’s nucleophilic assault. Next, electrophilic phenol substitution is followed by dehydration to produce intermediate (I). The NC protonated the generated intermediate (I), which subsequently underwent intermolecular esterification, ethanol elimination, and ring closure to yield the appropriate coumarin (Scheme 11e).
2.4. Synthesis of Oxazole/Isoxazoles
2.5. Synthesis of Pyrans
- Eshtehardian et al. used a green and simple method to produce MgFe2O4 NC, which they tested for the synthesis of 2-amino-7-hydroxy-4H-chromene and tetrahydrobenzo[b]pyran derivatives [103] (Scheme 20a). The proposed NC could be magnetically separated and reused four times without losing its catalytic activity. Based on mechanistic research, it was rationally assumed that Knoevenagel condensation of aldehyde and malononitrile formed an intermediate (I), which then proceeded through Michael addition with resorcinol to produce the adduct (II). To produce the corresponding product, this adduct might have undergone intramolecular cyclization followed by [1,3] H-shift (Scheme 20b). As a result, MgFe2O4’s Lewis acidic feature enabled Knoevenagel condensation and Michael addition by interacting with the aldehydic carbonyl O-atom and the cyanide group, respectively, and allowed the reaction to proceed successfully. As a result, the Lewis acidic feature of MgFe2O4 NC enhanced the Knoevenagel condensation and Michael addition by interacting with the aldehydic carbonyl O-atom and the cyanide group, respectively, and allowed the reaction to take place over its large surface area.
- Using a six-time-recoverable nickel ferrite NiFe2O4 NC, Pourshojaei et al. developed a one-pot cascade synthesis of 4H-chromenes [104] (Scheme 20a). The nanocatalyst’s amphoteric Lewis feature makes it useful for the fast synthesis of 4H-chromenes. According to a substrate scope investigation, the type of substituents on benzaldehyde had a significant impact on the effectiveness of the NC. The catalytic activity of the EWG was found to be higher than that of the ERG. According to the mechanistic findings, the Knoevenagel condensation between activated aldehydes and malononitrile first formed an intermediate (I), which then interacted with the activated dimedone and produced a new intermediate (II) after losing a water molecule. The newly created intermediate (II) was then subjected to intramolecular cyclization before being converted to the desired product via imine–enamine tautomerism (Scheme 20c).
- Singh et al. developed a magnetically retrievable amine-decorated SiO2@Fe3O4 hybrid NC (NH2@SiO2@Fe3O4) to carry out a solvent-free multicomponent synthesis of 2-amino-4H-benzo[b]pyran derivatives [105] (Scheme 20a). According to the data from the substrate scope study, the designed NC was tolerant of a wide variety of functional groups. According to mechanistic results, the proposed multicomponent method was initiated by the basic amino sites of the NC. The reaction began with the Knoevenagel condensation of malononitrile and aldehyde to produce arylidiene malononitrile, which was then Michael added to dimedone to produce an intermediate (I). To produce the intended product, this produced intermediate (I) was cyclized intramolecularly and then protonated (Scheme 20d). The hybrid NC has numerous notable characteristics, including durability, reusability, and recyclability for up to three reaction cycles, as well as a short reaction time and milder reaction conditions.
- Karami et al. developed a magnetic bifunctional (Fe3O4@SiO2@PTS-DABA) hybrid NC that was found to be catalytically effective for the synthesis of dihydropyranopyrazole [107] (Scheme 22a). According to the mechanistic findings, a pyrazolone ring was first generated by nanocatalyzed condensation between activated EAA and hydrazine hydrate, followed by dehydration and tautomerization. The Knoevenagel condensation of aldehyde and malononitrile created an intermediate (I), which interacted with pyrazolone to form the desired product by 6-exo-dig cyclization and tautomerization. It was discovered that the catalytic surface’s acidic and basic sites promoted intramolecular electrophilic cyclization via tautomerization (Scheme 22b). The features of the proposed process, such as quick synthesis, environmentally acceptable solvent, a five-time-recyclable catalyst, and the avoidance of caustic reagents, all make this technique appealing.
- In line with sustainable chemistry, Kamalzare et al. created a new magnetic biocomposite with chitosan and tannic acid (Fe3O4@chitosan-tannic acid) and used it in a cascade pyranopyrazole synthesis [108] (Scheme 22a). The observed hybrid NC had a high tolerance power for the benzaldehyde substituent pattern. According to one hypothesized mechanism, the proposed hybrid NC activated the carbonyl group of EAA and went through a nucleophilic assault of hydrazine to generate an intermediate, which was then subsequently attacked by another hydrazine molecule and eventually formed the pyrazolone ring (i) after losing water. The Knoevenagel condensation of aldehydes and malononitrile produced a novel intermediate (II), which was subsequently reacted with enolic pyrazolone to produce the desired product after significant intramolecular cyclization and tautomerization (Scheme 22c).
3. Conclusions and Future Perspectives
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Kumar, S.; Saroha, B.; Kumar, G.; Lathwal, E.; Kumar, S.; Parshad, B.; Kumari, M.; Kumar, N.; Mphahlele-Makgwane, M.M.; Makgwane, P.R. Recent Developments in Nanocatalyzed Green Synthetic Protocols of Biologically Potent Diverse O-Heterocycles—A Review. Catalysts 2022, 12, 657. https://doi.org/10.3390/catal12060657
Kumar S, Saroha B, Kumar G, Lathwal E, Kumar S, Parshad B, Kumari M, Kumar N, Mphahlele-Makgwane MM, Makgwane PR. Recent Developments in Nanocatalyzed Green Synthetic Protocols of Biologically Potent Diverse O-Heterocycles—A Review. Catalysts. 2022; 12(6):657. https://doi.org/10.3390/catal12060657
Chicago/Turabian StyleKumar, Suresh, Bhavna Saroha, Gourav Kumar, Ekta Lathwal, Sanjeev Kumar, Badri Parshad, Meena Kumari, Naveen Kumar, Mabel M. Mphahlele-Makgwane, and Peter R. Makgwane. 2022. "Recent Developments in Nanocatalyzed Green Synthetic Protocols of Biologically Potent Diverse O-Heterocycles—A Review" Catalysts 12, no. 6: 657. https://doi.org/10.3390/catal12060657
APA StyleKumar, S., Saroha, B., Kumar, G., Lathwal, E., Kumar, S., Parshad, B., Kumari, M., Kumar, N., Mphahlele-Makgwane, M. M., & Makgwane, P. R. (2022). Recent Developments in Nanocatalyzed Green Synthetic Protocols of Biologically Potent Diverse O-Heterocycles—A Review. Catalysts, 12(6), 657. https://doi.org/10.3390/catal12060657