2447-94-1Relevant academic research and scientific papers
Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones
Li, Zhiping,Luo, Yani,Lv, Leiyang,Nishihara, Yasushi,Tian, Tian
supporting information, p. 9276 - 9279 (2021/09/20)
A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.
Copper-catalyzed selective benzylic C-O cyclization of N-o-tolylbenzamides: Synthesis of 4 H-3,1-benzoxazines
Li, Yan,Li, Zhongshu,Xiong, Tao,Zhang, Qian,Zhang, Xiangyang
supporting information; body text, p. 3522 - 3525 (2012/08/08)
A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp3)-H over an aromatic C(sp 2)-H bond in N-o-tolylbenzamides is achieved.
Intramolecular charge transfer with N-benzoylaminonaphthalenes. 1-Aminonaphthalene versus 2-aminonaphthalene as electron donors
Zhang, Xuan,Liu, Chun-Hua,Liu, Li-Hong,Wu, Fang-Ying,Guo, Lin,Sun, Xiang-Ying,Wang, Chao-Jie,Jiang, Yun-Bao
, p. 728 - 732 (2007/10/03)
N-(substituted-benzoyl)-1-aminonaphthalenes and N-(substituted-benzoyl)-2-aminonaphthalenes (1-NBAs and 2-NBAs) with varied substituents at the para- or meta-position of benzoylphenyl ring were prepared to probe the difference between 1-aminonaphthalene (1-AN) and 2-aminonaphthalene (2-AN) as electron donors, using benzanilide-like charge transfer as a probe reaction. An abnormal long-wavelength emission was found for all of the prepared aminonaphthalene derivatives in cyclohexane and was assigned to the CT state by the observation of a substantial red shift with increasing solvent polarity or with increasing electron-withdrawing ability of the substituent. The CT emission energies were found to follow a linear relationship with the Hammett constant of the substituent and the value of the linear slope for 1-NBAs (-0.45 eV) was higher than that of 2-NBAs(-0.35 eV), the latter being close to that of the aniline derivatives (BAs, -0.345 eV). This pointed to a higher extent of charge separation in the CT state of 1-NBAs in which a full charge separation was established by the reduction potential dependence of the CT emission energy with a linear slope of -1.00. The possible contribution of the difference in the steric effect and the electron donating ability of the donors in 1-NBAs and 2-NBAs was ruled out by the observation that the corresponding linear slopes of benzoyl-substituted BAs remained unchanged when para-, meta-, ortho-, or ortho, ortho-methyls were introduced into the aniline moiety. It was therefore concluded that 1-AN enhanced the charge transfer in 1-NBAs and the proximity of its 1La and 1Lb states was suggested to be responsible. Results showed that the charge transfers in 1-NBAs and 2-NBAs were not the same and 1-AN and 2-AN as electron donors were different not only in electron donating ability but in shaping the charge transfer pathways as well.
Anticonvulsant activity of some 4-methoxy- and 4-chlorobenzanilides
Clark,McMillian
, p. 220 - 222 (2007/10/02)
A series of mono-, di-, and trimethylated derivatives of 4-chloro- and 4-methoxybenzanilide was synthesized and evaluated for anticonvulsant activity. This series was prepared in the course of studies designed to examine the relationship between anticonvulsant effects and benzamide structure. The compounds were tested in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazole (scMet), as well as with the rotorod assay for neurologic deficit. In mice dosed intraperitoneally, 4-methoxy-2, 6-dimethylbenzanilide (4) showed a median anticonvulsant potency (ED50) of 18.58 mg/kg in the MES test and a median toxicity (TD50) of 133.72 mg/kg in the rotorod toxicity assay, yielding a protective index (PI = TD50/ED50) of 7.2. In mice dosed orally with 4, the anti-MES ED50 was 27.40 mg/kg and the TD50 dose was determined to be 342.58 mg/kg, resulting in a protective index of 12.5.
