13466-30-3Relevant articles and documents
A convenient method for the preparation of N-unsubstituted hydrazones of aromatic ketones and aldehydes
Shirinian,Belen'kii,Krayushkin
, p. 2171 - 2172 (1999)
A general and useful method for the synthesis of N-unsubstituted hydrazones of aromatic ketones and aldehydes in good yields was elaborated. The use of a large excess of hydrazine hydrate and catalytic amounts of p-toluenesulfonic acid makes it possible to prepare the hydrazones without an admixture of the corresponding azine.
A novel transformation of oximes into hydrazones by hydrazine hydrate
Pasha,Nanjundaswamy
, p. 3827 - 3831 (2004)
We report a novel transformation of different substituted aryl, diaryl, and aralkyloximes into the respective hydrazones using hydrazine hydrate in ethanol at reflux in excellent yields.
Ancillary ligand-free copper catalysed hydrohydrazination of terminal alkynes with NH2NH2
Peltier, Jesse L.,Jazzar, Rodolphe,Melaimi, Mohand,Bertrand, Guy
, p. 2733 - 2735 (2016)
An efficient and selective Cu-catalysed hydrohydrazination of terminal alkynes with parent hydrazine is reported. The methodology tolerates a broad range of functional groups, allows for the synthesis of symmetrical and unsymmetrical azines, and can be extended to hydrazine derivatives and amines.
Structural basis of the substrate recognition of hydrazidase isolated from Microbacterium sp. strain HM58-2, which catalyzes acylhydrazide compounds as its sole carbon source
Akiyama, Tomonori,Ishii, Misaki,Takuwa, Atsushi,Oinuma, Ken-Ichi,Sasaki, Yasuyuki,Takaya, Naoki,Yajima, Shunsuke
, p. 1007 - 1012 (2017)
Hydrazidase was an enzyme that remained unidentified for a half century. However, recently, it was purified, and its encoding gene was cloned. Microbacterium sp. strain HM58-2 grows with acylhydrazides as its sole carbon source; it produces hydrazidase and degrades acylhydrazides to acetate and hydrazides. The bacterial hydrazidase belongs to the amidase signature enzyme family and contains a Ser-cisSer-Lys catalytic motif. The condensation of hydrazine and carbonic acid produces various hydrazides, some of which are raw materials for synthesizing pharmaceuticals and other useful chemicals. Although natural hydrazide compounds have been identified, the metabolic systems for hydrazides are not fully understood. Here, we report the crystal structure of hydrazidase from Microbacterium sp. strain HM58-2. The active site was revealed to consist of a Ser-cisSer-Lys catalytic triad, in which Ser179 forms a covalent bond with a carbonyl carbon of the substrate. 4-Hydroxybenzoic acid hydrazide bound to the S179A mutant, showing an oxyanion hole composed of the three backbone amide groups. Furthermore, H336 in the non-conserved region in the amidase family may define the substrate specificity, which was confirmed by mutation analysis. A wild-type apoenzyme structure revealed an unidentified molecule covalently bound to S179, representing a tetrahedral intermediate.
Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings
Lv, Leiyang,Li, Chao-Jun
, p. 2870 - 2875 (2021/03/14)
Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.
Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes
Campos-Dominguez, Emmanuel,Vasquez-Perez, Jose,Rojas-Lima, Susana,Lopez-Ruiz, Heraclio,Mendoza-Espinosa, Daniel
, (2020/12/07)
We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.
