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Synthesis of novel triarylmethane derivatives containing a trichloropyrimidine moiety

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Abstract

Firstly, the nucleophilic substitution reactions of 2,4,5,6-tetrachloropyrimidine (TCP) with hydroxybenzaldes 2a–c were employed to synthesize ((2,5,6-trichloropyrimidin-4-yl)oxy)benzaldehydes 3a–c. The fully characterization of the derived products clearly confirms that the nucleophilic attack of nucleophiles takes place at C-4 position of TCP, regioselectivity. Likewise, a clear preference for the nucleophilicity of 2a over 2b and 2c was observed in these reactions. Secondly, the solvent-less Friedel–Crafts alkylation reactions of arenes/heteroarenes with the derived aldehydes catalyzed by SiO2-H2SO4 were applied to synthesize a novel series of triarylmethane derivatives containing a trichloropyrimidine moiety. The chemical structures of all the compounds were elucidated by FT-IR, NMR spectra and elemental analyses.

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Scheme 1
Scheme 2
Scheme 3

Notes

  1. General procedure for the synthesis of (2,5,6-trichloropyrimidin-4-yl)oxybenzaldehydes 3a–c (Scheme 1): In a round-bottomed flask, a mixture of 2,4,5,6-tetrachloropyrimidine 1 (1 mmol), hydroxybenzaldehydes 2 (1 mmol) and K2CO3 (1.5 mmol) in CH3CN (5mL) was stirred at room temperature for appropriate time. The reaction mixture was poured on 10 mL water and extracted with EtOAc (3 × 10 mL). The organic layer was then dried over MgSO4 and solvent was evaporated. The residue was purified by recrystallization from EtOH to provide the pure products 3a–c.

  2. General procedure for the synthesis of triarylmethane derivatives containing perchloropyrimidine subunits 5a–k (Scheme 3: Silica-supported sulfuric acid (SiO2-H2SO4) was prepared following the procedure reported in the literature [96, 97]. A 25 mL round-bottomed flask equipped with a stir bar was charged with arene 5a–d (4 mmol), (2,5,6-trichloropyrimidin-4-yl)oxy)benzaldehyde 2 (1 mmol) and SiO2-H2SO4 (200 mg). The resulting mixture was heated at 80 °C for the allotted time. The progress of the reaction was monitored by n-Hexane/EtOAc (5:2) as eluent. After completion of the reaction, the mixture was cooled to room temperature and absolute EtOH (2 × 5 mL) was added. The catalyst was separated by simple filtration and the crude product was purified by plate chromatography using n-Hexane/EtOAc (5:2) as eluent to obtain the pure product 5a–k. The product 5l was also synthesized in a similar way under the optimized reaction conditions.

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Acknowledgements

We are grateful to the research council of the Vali-e-Asr University of Rafsanjan and Malek-Ashtar University of Technology for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Malek-Ashtar University of Technology, Shahin-Shahr, Islamic Republic of Iran

    Fatemeh Rezazadeh-Jabalbarezi & Fariborz Atabaki

  2. Department of Chemistry, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of Iran

    Fatemeh Rezazadeh-Jabalbarezi & Reza Ranjbar-Karimi

  3. NMR Laboratory, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, 77176, Islamic Republic of Iran

    Kazem Mohammadiannejad

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  1. Fatemeh Rezazadeh-Jabalbarezi
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  2. Reza Ranjbar-Karimi
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Correspondence to Reza Ranjbar-Karimi or Kazem Mohammadiannejad.

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Rezazadeh-Jabalbarezi, F., Ranjbar-Karimi, R., Mohammadiannejad, K. et al. Synthesis of novel triarylmethane derivatives containing a trichloropyrimidine moiety. J IRAN CHEM SOC 20, 2917–2922 (2023). https://doi.org/10.1007/s13738-023-02888-6

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