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Survey reaction of 2-amino-N-(aryl) benzimidamides with ninhydrin in different conditions and investigation of reaction mechanism using density functional theory (DFT)

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Abstract

In this investigation, firstly, 1-(2-amino-phenyl)-N-(aryl) methane diamine derivatives were synthesized by reaction of 2-aminobenzo nitrile with aromatic amines in the presence of aluminum chloride as the catalyst. Then, the reaction of these intermediates with ninhydrin in different conditions was investigated. The reaction between ninhydrin and 2-amino-N'-(aryl) benzimidamide derivatives in water as solvent under reflux conditions resulted in the synthesis of diazepine derivatives. The same results were obtained when the reaction was done in EtOH and in the presence of a few drops of sulfuric acid at room temperature. Also, this reaction was carried out in ethanol as solvent without the presence of sulfuric acid at room temperature which resulted in the synthesis of spiro [indene-2,2ʹ-quinazoline] derivatives. And finally, the reaction was carried out in ethanol as solvent without the presence of sulfuric acid at the reflux conditions which resulted in the synthesis of isoquinolino-quinazoline derivatives. These N-heterocycles compounds are important biologically. Mild reaction conditions, simple procedure and purification and also product diversity with changing conditions are important advantages of this method. Also, to better understanding reaction mechanism on the condensation reactions of 2-amino-N-(aryl) benzimidamides with ninhydrin in different conditions, density functional theory (DFT)-based quantum chemical methods have been applied. Calculated atomic charges suggest that the C-1 (+ 0.54 a.u.) center of ninhydrin is a better electrophile than C-2 (+ 0.42 a.u.) center.

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Acknowledgements

We are thankful to the Office of Graduate Studies of Vali-e-Asr University of Rafsanjan, for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, 77176, Rafsanjan, Iran

    Ali Darehkordi, Marziyeh Mohammadi, Kobra Sayyahi, Zahra Ahmadi, Fariba Rahmani & Farzaneh Nejadkhorasani

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  1. Ali Darehkordi
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  2. Marziyeh Mohammadi
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  3. Kobra Sayyahi
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Correspondence to Marziyeh Mohammadi.

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Darehkordi, A., Mohammadi, M., Sayyahi, K. et al. Survey reaction of 2-amino-N-(aryl) benzimidamides with ninhydrin in different conditions and investigation of reaction mechanism using density functional theory (DFT). Mol Divers 27, 59–70 (2023). https://doi.org/10.1007/s11030-022-10400-0

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  • DOI: https://doi.org/10.1007/s11030-022-10400-0

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