65124-88-1Relevant academic research and scientific papers
Cp*Co(III)-catalyzed C[sbnd]H amidation of azines with dioxazolones
Huang, Yanzhen,Pi, Chao,Tang, Zhen,Wu, Yangjie,Cui, Xiuling
supporting information, p. 3237 - 3240 (2020/09/15)
Cp*Co(III)-catalyzed direct C[sbnd]H amidation of azines has been developed. This conversion could proceed smoothly in the absence of external oxidants, acids or bases, with excellent regioselectivity and broad functional group tolerance. CO2 w
One-pot synthesis of [1,2,4]Triazolo[1,5-a]pyridines from azines and benzylidenemalononitriles via copper-catalyzed tandem cyclization
Lv, Jianguang,He, Zhiqing,Zhang, Jianmin,Guo, Yuwei,Han, Ziwei,Bao, Xinhua
supporting information, p. 3996 - 4004 (2018/06/20)
A simple and efficient copper-catalyzed tandem radical cyclization reaction has been discovered for the synthesis of triaryl [1,2,4]triazolo[1,5-a]pyridines from easily accessible azines and benzylidenmalononitriles. The new transformation involves multip
Rh-Catalyzed Regioselective ortho-C-H Carbenoid Insertion of Diarylazines
Yu, Yunliang,Kuai, Changsheng,Chauvin, Remi,Tian, Nian,Ma, Shuangshuang,Cui, Xiuling
, p. 8611 - 8616 (2017/08/23)
The Rh-catalyzed ortho-C-H carbenoid insertion reaction of diarylazines with diazo compounds has been developed. A wide range of ortho-substituted diarylazines have been obtained in moderate to high yields with high regioselectivity at room temperature. The hydrolysis of the products could release ketones or aldehydes, giving access to aromatic 1,5-keto-diesters as valuable synthons for further chemical transformations.
Rhodium(III)-catalyzed coupling of aromatic ketazines or oximes with 2-vinyloxirane via C-H activation
Wen, Jing,Wu, An,Miao, Yuqin,Zhu, Jin
supporting information, p. 5512 - 5516 (2015/09/21)
Described herein is a rhodium(III)-catalyzed coupling of aromatic ketazines or oximes with 2-vinyloxirane via directed C-H activation. This reaction proceeds efficiently under mild conditions with a low catalyst loading, especially in conditions with room temperature in the absence of additives for aromatic ketazines. A wide range of substituted substrates is supported and a possible mechanism is proposed according to the experimental results of kinetic isotopic effect, reversibility studies, and catalysis with rhodacycle intermediate c1.
Rh-catalyzed sequential oxidative C-H and N-N bond activation: Conversion of azines into isoquinolines with air at room temperature
Han, Wenjia,Zhang, Guoying,Li, Guangxing,Huang, Hanmin
supporting information, p. 3532 - 3535 (2014/07/21)
A rhodium-catalyzed sequential oxidative C-H annulation reaction between ketazines and internal alkynes has been developed via C-H and N-N bond activation with air as an external oxidant, which led to an efficient approach toward isoquinolines with high atom efficiency at rt. Utilizing the distinctive reactivity of this catalysis, both N-atoms of the azines could be efficiently incorporated to the desired isoquinolines under very robust and mild reaction conditions.
Ring and side chain formylated pyrazoles from acetophenone azines and Vilsmeier's reagent
Manikannan, Ramaiyan,Muthusubramanian, Shanmugam
experimental part, p. 671 - 677 (2011/07/07)
Differently substituted acetophenone azines on treatment with excess phosphorous oxychloride in N,N-dimethylformamide have found to yield three products in each case. An acceptable mechanism has been suggested for the formation of all the three products.
Evaluation of the extent of conjugation in symmetrical and asymmetrical aryl-substituted acetophenone azines using electrochemical methods
Sauro,Workentin
, p. 831 - 838 (2007/10/03)
The electrochemical behavior of a series of symmetrical and unsymmetrical aryl-substituted acetophenone azines (1-X/Y, where X and Y are 4-NO2, 4-CN, H, 3-OCH3, 4-OCH3, 4-CH3, and 4-N(CH3)2) was studied in acetonitrile and N,N-dimethylformamide (DMF) solution using cyclic voltammetry (CV). Compounds 1-X/Y, where neither X or Y are nitro substituents, undergo successive reduction to their radical anion (1-X/Y·-) and then dianion (1-X/Y2-), respectively. In all cases, the formation of the radical anion is completely reversible and the standard reduction potentials, E°1-X/Y/1-X/Y·- could be determined. The reversibility of the second electron transfer is substituent dependent with certain dianions sufficiently basic to be protonated under our conditions. Standard reduction potentials (E°1-X/Y/1-X/Y·-) for the formation of radical anions exhibit a large substituent effect with values differing by more than 0.66 V throughout the series going from 1-4-CN/4-CN to 1-4-OCH3/4-OCH3; similar substituent effects were determined for the formation of the dianion. The nitro-containing azines deviate from the above-mentioned behavior. With the exception of 1-4-NO2/4-NO2, they exhibit single electron waves that have values of E°1-X/Y/1-X/Y·- within 40 mV of each other and thus the reduction is not subject to the same substituent effect as the other azines. 1-4-NO2/4-NO2 exhibits an E° at a similar potential, but is a two-electron reversible wave with features indicative of a reduction system containing two localized, nonconjugated redox centers. The reduction potentials of all the aryl azines were correlated with Hammett σ parameters to look at variations in E°1-X/Y/1-X/Y·- vs SCE as a function of substituent. The small ρ values in combination with the other electrochemical data provide support for single bond character of the N-N bond and evidence for a lack of strong electronic communication between the two aryl centers through the azomethine bonds, especially for those systems with electron-withdrawing groups.
NOVEL OXIDATIVE CLEAVAGE OF CARBON-CARBON BOND IN HYDRAZONES BY OXYGENATION WITH COBALT SCHIFF BASE COMPLEX
Nishinaga, Akira,Yamazaki, Shigekazu,Matsuura, Teruo
, p. 2649 - 2652 (2007/10/02)
Oxygenation of aromatic ketone hydrazones with Co(salen) in methanol resulted unexpectedly in oxidative degradation to give methyl benzoate derivatives.A mechanism involving nucleophilic attack by methanol on a diazo intermediate is discussed.
A REINVESTIGATION OF THE SYNTHESIS OF 1,2-DIHYDRODIAZEPIN-3-ONES FROM PYRONES
Peet, Norton P.,Sunder, Shyam
, p. 393 - 399 (2007/10/02)
The reactions of 5-acetyl-6-hydroxy-4-(4-methoxyphenyl)-2H-pyran-2-one (5) and 4-(4-methoxyphenyl)-2H-pyran-2,6-dione (4) with hydrazine and phenylhydrazine respectively, gave the respective 1-amino-2-pyridones 8 and 11 rather than diazepinones 6 and 10,
SYNTHESIS AND MESOMORPHIC PROPERTIES OF THREE HOMOLOGOUS SERIES OF 4,4 prime -DIALKOXY- alpha , alpha prime -DIMETHYLBENZALAZINES.
Marcos,Melendez,Serrano
, p. 157 - 172 (2007/10/02)
Three homologous series of alpha , alpha prime -dimethylbenzalazines have been synthesized: 4,4 prime -dialkoxy- alpha , alpha prime -dimethylbenzalazines, 4,4 prime -dialkoxy-2,2 prime -dihydroxy- alpha , alpha prime -dimethylbenzalazines, and 4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines. The influence of molecular structure on the mesomorphic properties was studied. Mesomorphic properties and phase transitions were determined using a polarizing hot-stage microscope and a differential scanning calorimeter. The introduction of one or two hydroxyl groups in position 2- or 2-and 2 prime -of the aromatic rings (4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines and 4,4 prime -dialkoxy-2,2 prime -dihydroxy- alpha , alpha prime -dimethylbenzalazines respectively) gives molecules with an excellent mesogenic quality, and all the prepared compounds of these series exhibit mesomorphism. Compounds of the series with two hydroxyl groups exhibit smectic polymorphism which is not so in the case of the compounds of the other series. The melting temperatures are systematically lower for the 4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines than for the other two series.
