3084-52-4Relevant academic research and scientific papers
Preparation of halogen-containing 4H-pyrido[e][1,3]oxazin-4-ones and their transformation into 2-hydroxypyridinyl-substituted 1,2,4-oxadiazoles and 1,2,4-triazoles
Le Falher, Laetitia,Ben Ayad, Omar,Ziyaret, Ozge,Botuha, Candice,Thorimbert, Serge,Slowinski, Franck
, p. 3830 - 3840 (2015)
A complete study on the preparation of original halogen-containing 4H-pyrido[e][1,3]oxazin-4-ones and their transformation into 1,2,4-oxadiazoles and 1,2,4-triazoles is presented. Starting from pyridyl-imide sodium salts, the efficiency of the intramolecu
Design, synthesis, pharmacological evaluation, in silico modeling, prediction of toxicity and metabolism studies of novel 1-(substituted)-2-methyl- 3-(4-oxo-2-phenyl quinazolin-3(4H)-yl)isothioureas
Sulthana,Alagarsamy,Chitra
, p. 352 - 368 (2021/03/08)
Background: Although exhaustive efforts to prevent and treat tuberculosis (TB) have been made, the problem still continues due to multi-drug-resistant (MDR) and extensively drugresistant TB (XDR-TB). It clearly highlights the urgent need to develop novel
Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp2)?H Hydroxylation via Electro-chemical Oxidation
Wu, Hongfeng,An, Qi,He, Chaoyin,Fan, Xiaodong,Guo, Weihao,Zuo, Minghui,Xu, Chunzhao,Guo, Rui,Chu, Wenyi,Sun, Zhizhong
supporting information, p. 2459 - 2465 (2020/04/29)
An electrochemical direct ortho-hydroxylation of 2-aryl-4H-benzo[e][1,3]oxazin-4-ones was developed with Pd(OAc)2 as catalyst, oxazine ring as a directing group and Oxone as the hydroxylation reagent. A series of hydroxylation products were obtained under mild conditions, and the yields were from medium to good. This method is characterized by good functional group tolerance and a wide range of substrates. More importantly, use anodic oxidation to avoid the use of potentially toxic and polluting oxidants. A gram-scale direct electrochemical hydroxylation of 2-phenyl-4H-benzo[e][1,3]oxazin-4-one was performed, and the hydroxylation product was applied to synthesize the drug deferasirox. In addition, the single crystal of 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was obtained and determined by X-ray diffraction. Finally, the reaction mechanism was proposed and verified by cyclic voltammetry (CV). This protocol also provides an alternative electrochemical hydroxylation methodology for the functionalization of molecules. (Figure presented.).
Synthesis and biological evaluation of 1,2,4-triazole derivatives as potential neuroprotectant against ischemic brain injury
Chen, Jianwen,Jiang, Caibao,Lao, Yaoqiang,Li, Xinhua,Liang, Jie,Liao, Liping,Shi, Jinguo,Wang, Yang,Wen, Jin,Zhang, Jingxia,Zhou, Shujia
, (2020/02/15)
A series of 1,2,4-triazole derivatives 1–14 was synthesized to investigate their neuroprotective effects and mechanisms of action. Compounds 5–11 noticeably protected PC12 cells from the cytotoxicity of H2O2 or sodium nitroprusside (SNP). Compound 11 was the most effective derivative. Compound 11 chelated Fe (II) iron, scavenged reactive oxygen species (ROS), and restored the mitochondrial membrane potential (MMP). Moreover, it enhanced the activity of the antioxidant defense system by increasing the serum level of superoxide dismutase (SOD) and promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2). Compound 11 caused certain improvements in behavior, the cerebral infarction area, and serum levels of biochemical indicators (TNF-α, IL-1β, SOD and MDA) in a rat MCAO model. The lethal dose (LD50) of compound 11 in mice receiving intraperitoneal injections was greater than 400 mg/kg. Meanwhile, pharmacokinetic experiments revealed high bioavailability of this compound after both oral and intravenous administration (F = 60.76%, CL = 0.014 mg/kg/h) and a longer half-life (4.26 and 5.11 h after oral and intravenous administration, respectively). Based on these findings, compound 11 may be a promising neuroprotectant for the treatment of ischemic stroke.
Chemoselective reaction of benzoylisothiocyanates with hydroxyl group of salicylamide: A new and convenient entry into 2-Aryl-4 H -benzo[e][1,3]oxazin-4- ones
Singh, Tarjeet,Singh, Girija S.,Lakhan, Ram
, p. 1442 - 1448 (2013/10/08)
The reactions of benzoylisothiocyanates with salicylamide in pyridine-xylene solution occurs chemoselectively at the hydroxyl group of the salicylamide to afford the corresponding O-benzoyl derivatives. The latter products, on prolonged heating in pyridin
Evaluation of antibacterial activity of novel quinazoline derivatives
Tiwari, Ravi,Chhabra, Gurmeet
experimental part, p. 5981 - 5986 (2010/12/24)
In the present study, a series of novel quinazoline derivatives were synthesized by condensation with different aromatic amines via cyclized intermediate 2-phenyl-1,3-benzoxazin-4-one. The chemical structures were confirmed by means of IR and 1H NMR. These compounds were screened for antibacterial (Staphylococcus aureus ATCC-9144, Escherichia coli ATCC-25922, activities by paper disc diffusion technique. The potency of antibiotic content in samples can be determined by chemical, physical or biological means. An assay is made to determine the ability of an antibiotic to kill or inhibit the growth of living microorganism. The inhibition of microbial growth under standardized conditions may be utilized for demonstrating the therapeutic efficacy of drugs. Microorganism employed in biological assay are of various typesbacteria for amino acid, antibiotics, fungi for vitamins, trace elements, antibiotics and fungicidal and fungi static materials. The synthesized compounds were evaluated for antibacterial activity. Some of these synthesized compounds shown significant antibacterial activity.
Catalytic flash vacuum pyrolysis (CFVP): A new way to afford 7H-dibenzo[b,d]azepin-7-one
Moyano, Elizabeth L.,Eimer, Griselda A.,Lucero, Paola L.,Chanquia, Corina M.,Herrero, Eduardo R.,Yranzo, Gloria I.
scheme or table, p. 98 - 103 (2010/10/02)
Catalytic flash vacuum pyrolysis (cfvp) of 2-(1H-1,2,3-benzotriazol-1-yl)-phenylethanone (1) was performed over different mesoporous solids of the MCM-41 type: pure Si-MCM-41, Al-MCM-41 and Ti-MCM-41 with Si/metal ratio equal to 20 and 120. While in the absence of the catalyst (conventional fvp) the thermal reaction afforded 7H-dibenzo[b,d]azepin-7-one (5) as the main product between 400 and 500 °C, in the cfvp systems different products were obtained between 350 and 450 °C depending on the type of catalysts. Al-MCM-41 showed the best catalytic performance with azepinone selectivity of 87% at 450 °C. The mechanisms of formation of these different products as well as the effect of different solids are discussed. Mesoporous materials used in this study have been prepared by direct hydrothermal synthesis. Structural regularity was determined by XRD and highly ordered structures were obtained.
Process for the production of benzoxazinones
-
, (2008/06/13)
There is described a process for the production of a 1,3-benzoxazin-4-one having the formula: in which R1 and R2, independently, are hydrogen, cyano, halogen, nitro, C1-C20alkyl, O-C1-C20alkyl, phenyl, NH-CO-C1-C20alkyl, N(R3)2, SO2N(R3)2, COOR3 or CON(R3
Synthesis of 2-Methyl-4H-1,3-benzoxazin-4-ones and Related Compounds
Stegmann, Hartmut B.,Klotz, Dieter,Weiss, Joachim E.
, p. 4632 - 4636 (2007/10/02)
4H-1,3-benzoxazin-4-ones 2 are smoothly prepared via (acylimino)phosphoranes 1 by intramolecular condensation analogous to a Wittig reaction.Tert. phosphanes are used for the preparation of the (acylimino)phosphoranes 1 which are converted into the corresponding benzoxazines and tert. phosphane oxides, e.g. 2-methyl-4H-1,3-benzoxazin-4-one (2a) which, in spite of some attempts, has not been obtained before.
