101714-47-0Relevant articles and documents
Continuous synthetic method of 1, 2, 3-triazole compound
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Paragraph 0063-0065, (2019/07/11)
The invention provides a continuous synthetic method of a 1, 2, 3-triazole compound. The continuous synthetic method comprises following steps: reaction raw materials containing an azide compound andacetylene are introduced into a continuous reaction equi
Elucidation of the E-Amide Preference of N-Acyl Azoles
Takahashi, Yuka,Ikeda, Hirotaka,Kanase, Yuki,Makino, Kosho,Tabata, Hidetsugu,Oshitari, Tetsuta,Inagaki, Satoshi,Otani, Yuko,Natsugari, Hideaki,Takahashi, Hideyo,Ohwada, Tomohiko
, p. 11370 - 11382 (2017/11/10)
The conformational properties of N-acyl azoles (imidazole, pyrazole, and triazole) were examined. The N-2′,4′,6′-trichlorobenzoyl azoles were stable in methanol at room temperature, and no hydrolyzed products were observed over 7 days in the presence of 5% trifluoroacetic acid or 5% triethylamine in CDCl3. The high stability may be explained by the double-bond amide character caused by the steric hindrance due to the ortho-substituents in the benzoyl group. While specific E-amide preferences were observed in N-acyl pyrazoles/triazoles, the amides of the imidazoles gave a mixture of E and Z. One of the conceivable ideas to rationalize this conformational preference may be repulsive interaction between two sets of lone-pair electrons on the pyrazole 2-nitrogen (nN) and the carbonyl oxygen atoms (nO) in the Z-conformation of N-acyl pyrazoles/triazoles. However, analysis of orbital interactions suggested that in the case of the E-conformation of N-acyl pyrazoles, such electron repulsion is small because of distance. The interbond energy calculations suggested that the Z-conformer is involved in strong vicinal σ-σ repulsion along the amide linkage between the σN1N2 and σC1C2 orbitals in the anti-periplanar arrangement and between the σN1C5 and σC1C2 orbitals in the syn-periplanar arrangement, which lead to the overwhelming E-preference in N-acyl pyrazoles/triazoles. In the case of N-acyl imidazoles, similar vicinal σ-σ repulsions were counterbalanced, leading to a weak preference for the E-conformer over the Z-conformer. The chemically stable and E-preferring N-acyl azoles may be utilized as scaffolds in future drug design.
Process for the preparation of acylated cyclic 1,3-dicarbonyl compounds
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, (2008/06/13)
A process for preparing a compound of Formula (I); where Q completes an optionally substituted 5-or 6-member saturated carbocyclic ring and R is optionally substituted phenyl or optionally substituted C3-C6 cycloalkyl which comprises the rearrangement of a compound of Formula (II); where Q and R are as defined in relation to Formula (I) in a polar aprotic, dipolar aprotic or aromatic hydrocarbon solvent in the presence of a moderate base and an azole.
