We reported herein efficient economic high-pressure synthesis procedures for the synthesis of bis(azoles) and bis(azines) by utilizing the bis(enaminone) intermediate. Bis(enaminone) reacted with hydrazine hydrate, hydroxylamine hydrochloride, guanidine hydrochloride, urea, thiourea, and malononitrile to form the desired bis azines and bis azoles. A combination of elemental analyses and spectral data was used to confirm the structures of the products. Compared with conventional heating, the high-pressure Q-Tube method promotes reactions in a short period of time and provides high yields.
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http://dx.doi.org/10.3390/molecules28052355 | DOI Listing |
Molecules
March 2023
Department of Chemistry, College of Science, University of Jeddah, Jeddah 21589, Saudi Arabia.
We reported herein efficient economic high-pressure synthesis procedures for the synthesis of bis(azoles) and bis(azines) by utilizing the bis(enaminone) intermediate. Bis(enaminone) reacted with hydrazine hydrate, hydroxylamine hydrochloride, guanidine hydrochloride, urea, thiourea, and malononitrile to form the desired bis azines and bis azoles. A combination of elemental analyses and spectral data was used to confirm the structures of the products.
View Article and Find Full Text PDFOrg Lett
December 2022
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, P. R. China.
A new class of Michael acceptor, tetrazolyl-trifluoromethyl alkenes, has been discovered. They readily undergo Michael-type addition instead of addition-elimination reaction with aliphatic amines and azoles to furnish β-trifluoromethyl alkylamines and CF-substituted 1,2-bisazole derivatives, respectively. Additionally, some of the products are capable of engaging in microwave-assisted intramolecular denitrogenative annulation, leading to the formation of CF-substituted 1,4,5,6-tetrahydro-1,2,4-triazines that are otherwise difficult to access by other methodologies.
View Article and Find Full Text PDFChemistry
July 2015
Institute of Advanced Materials (INAM), Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain).
A rational synthetic procedure for the preparation of a series of pyrene-based neutral and dicationic bis-azole compounds is reported. The method allows the tailored design of pyrene-based azoles with different substituents at the nitrogen atoms of the heterocycles, for which the relative conformation of the resulting bis-azoles can be easily controlled. The bis-azoliums were used for the preparation of the related diplatinum complexes by reaction with [{Pt(ppy)(μ-Cl)2 }2 ] (ppy=2-phenylpyridinate).
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2015
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343 (USA).
Using a variety of functionalization strategies, derivatives of 4, 4'-bis(5-nitro-1,2,3-2H-triazole) were designed, synthesized, and characterized. The isomers were separated, their structures were confirmed with single-crystal X-ray analysis, and their properties were determined by differential scanning calorimetry, density, impact sensitivity, heat of formation, and detonation velocity and pressure (calculated by EXPLO5 V6.01).
View Article and Find Full Text PDFAngew Chem Int Ed Engl
April 2015
Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501 (Japan).
Winding vine-shaped molecular asymmetry is induced by enantioselective ring-closing metathesis with a chiral molybdenum catalyst. The reaction proceeds under mild conditions through an E-selective ring-closing metathesis leading to macrocyclic bisazoles with enantioselectivities of up to 96% ee.
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