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Calcium mediated efficient synthesis of N-arylamidines from Organic Nitriles and Amines

Abstract

Amidines are preeminent categories of organic compounds having wide applications in various industries. Here, we have developed a simple one-step reaction protocol for the facile synthesis of N-arylamidines catalysed by group calcium bis(hexamethyldisilazide) [Ca{N(SiMe3)2}2(THF)2]. The amidine synthesis was readily achieved from organic nitriles and amines which provided a broad substrate scope ranging from electron-withdrawing to electron-donating as well as heterocyclic substitution. The reaction was carried out in a solvent-free medium under ambient conditions. The nucleophilic addition of the aromatic amines to the aryl nitriles acquired good to excellent yields of the corresponding amidines. The reactivity of the amidines was further examined and the respective urea derivatives were achieved in excellent yield. The plausible mechanism involves the generation of an active calcium amido pre-catalyst that helps in the activation of the nitriles in the reaction course.

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Supplementary files

Article information


Submitted
18 Apr 2020
Accepted
18 May 2020
First published
18 May 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Calcium mediated efficient synthesis of N-arylamidines from Organic Nitriles and Amines

T. K. Panda, I. Banerjee and S. Sagar, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/D0OB00805B

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