An Efficient Synthesis of Spiro-Pyrimidines Derivatives Containing a Sulfonyl Scaffold

Title:An Efficient Synthesis of Spiro-Pyrimidines Derivatives Containing a Sulfonyl Scaffold

Volume: 14 Issue: 8

Author(s): Manijeh Nematpour*, Samira Rasouli Kohi, Elahe Abedi and Mahbob Lotfi

Affiliation:

• Young Researchers and Elites Club, Science and Research Branch, Islamic Azad, University, Tehran,Iran

Keywords: Sulfonyl-spiro-pyrimidines, sodium arylsulfinates, malononitrile, isatin, trichloroacetonitrile, primary amines.

Abstract: Background: A useful and simple strategy for the synthesis of sulfonyl-spiro-pyrimidines derivatives via a five-component reaction between sodium arylsulfinates, trichloroacetonitrile, primary amines, isatin and malononitrile in the DMF at room temperature is described in this study.

Methods: Initially, we performed the five-component reaction of trichloroacetonitrile, benzylamine, sodium arylsulfinate, isatin and malononitrile as a simple model, and then we optimized the reaction conditions by changing the solvent. DMF proved to be the most optimal solvent with highest yield for this reaction compared to MeOH, EtOH, MeCN, CH₂Cl₂, acetone, and tetrahydrofuran (THF). Therefore, the reaction was carried out in DMF at room temperature for 7 h, by using 1 mmol of benzylamine, 1 mmol of sodium arylsulfinate, 1 mmol of trichloroacetonitrile, 1.5 mmol of isatin, and 1.5 mmol of malononitrile. Under these conditions, functionalized sulfonyl-spiro-pyrimidines was indeed obtained with 89% yield.

Results: Using the optimized conditions described above, various sulfonyl-spiro-pyrimidines derivatives were synthesized from sodium arylsulfinates, malononitrile, isatin, trichloroacetonitrile, and various benzylamines with various electron-withdrawing or electron-donating substituents on the aromatic rings in DMF at room temperature.

Conclusion: In summary, the one-pot tandem reaction of benzylamine, sodium arylsulfinate, trichloroacetonitrile, isatin and malononitrile in DMF at room temperature led to the formation of functionalized sulfonyl-spiro-pyrimidines in good yields. The procedure described here has the advantage that the reaction is mild and fairly general, thus providing a useful path for the synthesis of functionalized spiro systems containing various sulfonyl groups.

Cite this article as:

Nematpour Manijeh*, Kohi Rasouli Samira, Abedi Elahe and Lotfi Mahbob, An Efficient Synthesis of Spiro-Pyrimidines Derivatives Containing a Sulfonyl Scaffold, Letters in Organic Chemistry 2017; 14 (8) . https://dx.doi.org/10.2174/1570178614666170426162522

DOI https://dx.doi.org/10.2174/1570178614666170426162522	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255