Publication Type Journal Article
Title 3-Dialkylamino-1,2,4-triazoles via Zn-II-Catalyzed Acyl Hydrazide-Dialkylcyanamide Coupling
Authors Sevilya N. Yunusova Dmitrii S. Bolotin Vitalii V. Suslonov Mikhail A. Vovk Peter M. Tolstoy V. Yu. Kukushkin
Groups CCC
Journal ACS OMEGA
Year 2018
Month July
Volume 3
Number 7
Pages 7224-7234
Abstract Zinc(II)-catalyzed (10 mol \% ZnCl2) coupling of acyl hydrazides and dialkylcyanamides in ethanol leads to 3-dialkylamino-1,2,4-triazoles (76-99\%; 17 examples). This reaction represents a novel, straightforward, and high-yielding approach to practically important 3-NR2-1,2,4-triazoles, which utilizes commercially available and/or easily generated substrates. Seventeen new 3-NR2-1,2,4-triazoles were characterized by HRESI+-MS and IR, H-1, and C-13\1H\ NMR spectroscopies and five species additionally by single-crystal X-ray diffraction (XRD). The Zn-II-catalyzed reaction proceeds via initial generation of the [Zn\RC(=(O) under bar) NH (N) under barH(2)\(3)](ZnCl4) complexes (exemplified by isolation of the complex with R = Ph, 76\%; characterized by HRESI+-MS, IR, CP-MAS TOSS C-13\H-1\ NMR, and XRD). Electronic effects of substituents at the acyl hydrazide moiety do not significantly affect the reaction rate and the yield of the target triazoles, whereas the steric hindrances reduce the reaction rate without affecting the yield of the heterocycles.
DOI http://dx.doi.org/10.1021/acsomega.8b01047
ISBN
Publisher
Book Title
ISSN 2470-1343
EISSN
Conference Name
Bibtex ID ISI:000438908600012
Observations
Back to Publications List