530-50-7Relevant articles and documents
Evidence for involvement of liver aldehyde oxidase in reduction of nitrosamines to the corresponding hydrazine
Tatsumi,Yamada,Kitamura
, p. 764 - 767 (1983)
-
Arylhydrazine trapping of benzynes: Mechanistic insights and a route to azoarenes
Sneddon, Dorian S.,Hoye, Thomas R.
, p. 3432 - 3436 (2021)
Arylhydrazines (ArNαHNβH2) are ambident nucleophiles. We describe here their reactivity with benzynes generated in situ by thermal cyclization of several multiynes. Products arising from attack of both the alpha- and beta-nitrogen atoms are observed. These competitive modes of reaction were explored by DFT calculations. Substituent effects on the site-selectivity for several substituted phenylhydrazines were explored. Interestingly, the hydrazo products from beta-attack (ArNHNHAr') can be oxidized, sometimes in situ by oxygen alone, to give structurally complex, unsymmetrical azoarenes (ArN=NAr'). Toluenesulfonohydrazide and benzohydrazide analogues were each demonstrated to undergo similar transformations, including oxidation to the corresponding benzyne-trapped azo compounds.
Palladium-catalyzed monoarylation of arylhydrazines with aryl tosylates
Huang, Yange,Choy, Pui Ying,Wang, Junya,Tse, Man-Kin,Raymond Wai-Yin Sun,Albert Sun-Chi Chan,Kwong, Fuk Yee
, p. 14664 - 14673 (2020/12/29)
A palladium-catalyzed C-N bond coupling reaction between arylhydrazines and aryl tosylates for facile synthesis of unsymmetrical N,N-diarylhydrazines has been developed. Employing the catalyst system of Pd(TFA)2 associated with newly developed phosphine ligand L1, the monoarylation of arylhydrazine proceeds smoothly to afford desired products in good-to-excellent yields (up to 95%) with good functional group compatibility. This method provides an alternative synthetic pathway for accessing structurally diversified N,N-diarylhydrazines from simple and easily accessible coupling components.
Preparation method of 9-anthraldehyde-1, 1-diphenylhydrazone
-
Paragraph 0030; 0034; 0035; 0038; 0041; 0045; 0049; 0053, (2017/02/24)
The invention relates to a preparation method of 9-anthraldehyde-1, 1-diphenylhydrazone. The preparation method comprises that anthracene, phosphorous oxychloride and N, N-dimethyl formamide are added into a reaction container, the materials undergo a reaction at a temperature of 60-120 DEG C for 6-48h to produce 9-anthraldehyde, N-nitrosodiphenylamine, zinc, acetate acid gracial and an alcohol solvent are added into the reaction container, the mixture undergoes a reaction at a temperature of 0-40 DEG C for 1-9h to produce 1, 1-diphenylhydrazine, 9-anthraldehyde and 1, 1-diphenylhydrazine are added into the reaction container, the mixture undergoes a reaction, the reaction product is cooled and precipitated, and the crystals are filtered and then are recrystallized in benzene so that 9-anthraldehyde-1, 1-diphenylhydrazone is obtained. Through simple recrystallization of the desired compound, a product with purity greater than 99.5% is obtained. The preparation method has the advantages of low raw material cost, mild reaction conditions and high desired product yield. The preparation method provides possibility for use of the hydrazone compound as a semi-conducting material in research on organic electroluminescent devices and organic light conductors.