Author:
Abbasi Fatemeh,Sardarian Ali Reza
Abstract
AbstractIn the current report, we introduce a simple, mild efficient and green protocol for N-formylation and N-acetylation of anilines using formamide, formic acid, and acetic acid as inexpensive, nontoxic, and easily available starting materials just with heating along stirring in [ChCl][ZnCl2]2 as a durable, reusable deep eutectic solvent (DES), which acts as a dual catalyst and solvent system to produce a wide range of formanilides and acetanilides. Also, a variety of unsymmetrical urea derivatives were synthesized by the reaction of phenyl isocyanate with a range of amine compounds using this benign DES in high to excellent yields. [ChCl][ZnCl2]2 showed good recycling and reusability up to four runs without considerable loss of its catalytic activity.
Publisher
Springer Science and Business Media LLC
Reference114 articles.
1. Carey, J. S., Laffan, D., Thomson, C. & Williams, M. T. Analysis of the reactions used for the preparation of drug candidate molecules. Org. Biomol. Chem. 4, 2337–2347. https://doi.org/10.1039/B602413K (2006).
2. Chen, J., Jia, J., Guo, Z., Zhang, J. & Xie, M. NH4I-promoted N-acylation of amines via the transamidation of DMF and DMA under metal-free conditions. Tetrahedron Lett. 60, 1426–1429. https://doi.org/10.1016/j.tetlet.2019.04.040 (2019).
3. Ghosh, T., Jana, S. & Dash, J. KOtBu-promoted transition-metal-free transamidation of primary and tertiary amides with amines. Org. Lett. 21, 6690–6694. https://doi.org/10.1021/acs.orglett.9b02306 (2019).
4. Greenberg, A., Breneman, C. M. & Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science (Wiley, 2000).
5. Cupido, T., Tulla-Puche, J., Spengler, J. & Albericio, F. The synthesis of naturally occurring peptides and their analogs. Curr. Opin. Drug discov. Dev. 10, 768–783 (2007).