Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation

Bhuyan, Pubanita; Bhorali, Pratiksha; Islam, Imdadul; Bhuyan, Amar Jyoti; Saikia, Lakhinath

doi:10.1016/j.tetlet.2018.03.032

Cited by 27 publications

(13 citation statements)

References 47 publications

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“…CuFe 2 O 4 catalyst system used for the purpose was prepared as discussed in our recent work by combined sonochemical and co‐precipitation technique. [ 53 ] Characterization of the catalyst was done using electron dispersive X‐ray (EDX) analysis, Fourier‐transform‐infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometer (VSM) study, and X‐ray photoelectron spectroscopy (XPS). SEM‐EDX spectrum (Figure 1c) ascertains the elemental presence of Cu, Fe, and O in 12.95, 29.48, and 57.57 atomic% respectively in the prepared sample.…”

Section: Resultsmentioning

confidence: 99%

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Bhuyan

Boruah

et al. 2020

Applied Organom Chemis

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In recent years, magnetically active CuFe2O4 nanoparticles have been gaining significant interest in the field of heterogeneous catalysis as those can be easily prepared and effortlessly recovered from a reaction system. Here, we are reporting our work on cascade syntheses of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones starting from 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil, aromatic aldehydes and nitromethane using magnetically active CuFe2O4 catalyst system under microwave irradiation and solvent‐less condition. The current methodology is a valued addition to the existing procedures of 5‐arylpyrido[2,3‐d]pyrimidines syntheses making best use of the diene behavior of 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil. However, heterogeneous catalysis has been employed for the first time to do the syntheses by carrying out [4 + 2]cycloaddition reaction between 6‐[(dimethylamino)methylene‐amino]‐1,3‐dimethyluracil and in situ generated 2‐(2‐nitrovinyl)arenes/heteroarenes. The methodology is highly time‐economic, and along with other features like easy recovery and good reusability of the catalyst, simple operating procedure, wide substrate scope, and good to excellent product yield, it offers the chemists a reaction protocol worth trying for the syntheses of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones. While laboratory prepared catalyst system was characterized using FT‐IR, XRD, SEM‐EDX, VSM, XPS and TEM analysis, all the synthesized compounds have been characterized using 1H and 13C NMR spectroscopy and HRMS.

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Section: Resultsmentioning

confidence: 99%

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Bhuyan

Boruah

et al. 2020

Applied Organom Chemis

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“…Optimization of the reaction condition was started by taking B(C 6 F 5 ) 3 as the catalyst system (Table , Entry 1–7) as it had already been established as a very efficient catalyst for Michael addition reaction of N , N ‐dialkylaniline with α , β ‐unsaturated carbonyl compounds . Ability of microwave irradiation in reducing reaction time and our earlier experiences in microwave chemistry insisted us to explore the reactions under microwave irradiation . Among the solvents tested, CHCl 3 was observed as the most promising one resulting 3 a in 65% yield within 10 minutes (Table , Entry 1) while PhCH 3 came next to it (51%, Entry 2).…”

Section: Resultsmentioning

confidence: 99%

Fe(OTf)₃: An Efficient Catalyst for Michael Addition Reactions of Homoaromatic C‐H Nucleophiles with Nitrostyrenes under Microwave Irradiation in Solvent‐Free Condition

Bhuyan¹,

Bhuyan²,

Nyodu³

et al. 2019

ChemistrySelect

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Available procedures for Michael addition reaction of homoaromatic C−H nucleophiles (N,N‐dialkylanilines and their cyclic analogues) with nitrostyrenes are observed to be very time consuming (18‐72 h). So, a gentle effort has been made to reduce the time requirement, which is reported herein. Our developed methodology makes use of commercially available Fe(OTf)3 as an efficient catalyst (5 mol%) under microwave irradiation (700 W, 120 °C) and solvent‐free condition and found to be capable of furnishing the Michael adducts in 40–98% yields within 10–20 minutes (19 examples). The regioselectivity of addition of N,N‐dialkylanilines and their cyclic analogues to nitrostyrene derivatives is observed to be exclusively para. The methodology can be extended to the use of cinnamaldehyde as Michael acceptor (2 examples). Three of our Michael addition products are denitrohydrogenated to achieve their corresponding alkylated arenes which paves an effective two‐step synthetic route for p‐alkylated N,N‐dilalkylanilines. Ability to reduce the time requirement by a huge margin (from days to minutes), exclusion of solvent system, exclusive para addition of the homoaromatics to nitrostyrenes are the features of attraction of the developed methodology. The proposed two‐step procedure for regioselective synthesis of p‐alkylated N,N‐dialkylanilines should attract readers’ attention.

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“…1,4‐Di(1 H ‐1,2,3‐triazol‐4‐yl)benzene (2j): (Table ): Off‐white solid (210.09 mg, 99 %). 1 H NMR (400 MHz, CDCl 3 + [D 6 ]DMSO): δ = 14.91 (br.…”

Section: Methodsmentioning

confidence: 99%

Facile Synthesis of 1,3,5‐Triarylbenzenes and 4‐Aryl‐NH‐1,2,3‐Triazoles Using Mesoporous Pd‐MCM‐41 as Reusable Catalyst

Saha

Peng

et al. 2018

Eur J Org Chem

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We report mesoporous nano‐Pd‐MCM‐41 catalyzed rapid and efficient synthesis of 1,3,5‐triarylbenzenes via de‐nitrative cyclotrimerization of β‐nitrostyrenes. All the reactions were very fast and high yielding. The Pd‐MCM‐41 was also very effective in catalyzing de‐nitrative [3+2] cycloaddition of β‐nitrostyrenes with TMSN3 to synthesize 4‐aryl‐NH‐1,2,3‐triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.

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Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation

Cited by 27 publications

References 47 publications

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Fe(OTf)₃: An Efficient Catalyst for Michael Addition Reactions of Homoaromatic C‐H Nucleophiles with Nitrostyrenes under Microwave Irradiation in Solvent‐Free Condition

Facile Synthesis of 1,3,5‐Triarylbenzenes and 4‐Aryl‐NH‐1,2,3‐Triazoles Using Mesoporous Pd‐MCM‐41 as Reusable Catalyst

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Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation

Cited by 27 publications

References 47 publications

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Magnetically recoverable copper ferrite catalyzed cascade synthesis of 1,3‐dimethyl‐6‐nitro‐5‐arylpyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones under microwave irradiation and solvent‐less condition

Fe(OTf)3: An Efficient Catalyst for Michael Addition Reactions of Homoaromatic C‐H Nucleophiles with Nitrostyrenes under Microwave Irradiation in Solvent‐Free Condition

Facile Synthesis of 1,3,5‐Triarylbenzenes and 4‐Aryl‐NH‐1,2,3‐Triazoles Using Mesoporous Pd‐MCM‐41 as Reusable Catalyst

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Fe(OTf)₃: An Efficient Catalyst for Michael Addition Reactions of Homoaromatic C‐H Nucleophiles with Nitrostyrenes under Microwave Irradiation in Solvent‐Free Condition