250602-56-3Relevant academic research and scientific papers
Cyanuric chloride as a mild and active Beckmann rearrangement catalyst
Furuya, Yoshiro,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 11240 - 11241 (2005)
The first general organocatalytic Beckmann rearrangement of ketoximes into amides has been realized by the catalytic use of cyanuric chloride. Furthermore, acids such as HCl and ZnCl2 are effective as cocatalysts with cyanuric chloride. For example, azacyclotridecan-2-one, which is synthetically useful as a starting material for nylon-12, was prepared in quantitative yield by the Beckmann rearrangement of cyclododecanone oxime (100 mmol scale) catalyzed by cyanuric chloride (0.5 mol %) and ZnCl2 (1 mol %). Copyright
Synthesis and elastase inhibition activities of novel aryl, substituted aryl, and heteroaryl oxime ester derivatives
Hasdemir, Belma,Sacan, Ozlem,Yasa, Hasniye,Kucuk, Hatice B.,Yusufoglu, Ayse S.,Yanardag, Refiye
, (2018)
Fifteen novel aryl, substituted aryl and heteroaryl γ-hydroxy- (2a–e), γ-methoxyimino- (3a–e), and γ-benzyloxyimino- (4a–e) butyric acid methyl esters were investigated for their enzyme inhibition, and the synthesis of 10 compounds (3a–e, 4a–e) is given in this study. The other five compounds (2a–e) were synthesized before in another study. Compounds 3a–e and 4a–e were synthesized in this work as original compounds and characterized by 1H and 13C NMR, IR, mass, and elemental analyses. Their (E/Z)-isomerisation ratios were analyzed by 1H and 13C NMR. All of them are of pure (E)-configuration. Due to the literature survey, the elastase inhibition activity was not studied for these compounds. Elastase inhibition ability was investigated in this work for five γ-hydroxy- (2a–e), five γ-methoxy- (3a–e), and five γ-benzyloxyimino- (4a–e) butyric acid methyl esters. All these 15 compounds showed elastase inhibition activity. Compound 2b was the best one and exhibited a better activity than the standard ursolic acid whereas compound 2a worked like the standard. All these compounds can be novel elastase inhibitor agents in the pharmaceutical and cosmetic industries.
Design and synthesis of novel bis-oximinoalkanoic acids as potent PPARα agonists
Pingali, Harikishore,Jain, Mukul,Shah, Shailesh,Zaware, Pandurang,Makadia, Pankaj,Pola, Suresh,Thube, Baban,Patel, Darshit,Patil, Pravin,Priyadarshini, Priyanka,Suthar, Dinesh,Shah, Maanan,Giri, Suresh,Patel, Pankaj
, p. 1156 - 1161 (2010)
Bis-oximinoalkanoic acid derivatives were designed and synthesized to aid in the characterization of selective PPARα agonists by replacing the oxazole ring with flexible oximino group in the lipophilic tail part of a previously reported compound 3. Selected compounds 9d and 9m showed excellent potency and high selectivity towards PPARα in vitro. These compounds found effective in reducing serum triglycerides (TG) in vivo.
Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Gao, Yu,Liu, Jingjing,Li, Zhenjiang,Guo, Tianfo,Xu, Songquan,Zhu, Hui,Wei, Fulan,Chen, Siming,Gebru, Hailemariam,Guo, Kai
, p. 2040 - 2049 (2018/02/23)
A novel protocol for the activation of the Beckmann rearrangement utilizing the readily available and economical geminal dichloroimidazolidinediones (DCIDs) on a substoichiometric scale (10 mol %) has been developed. A unique self-propagating mechanism for the substoichiometric dichloroimidazolidinedione-activated transformation was proposed and validated. The substrate scope of the developed protocol has been demonstrated by 23 examples with good to excellent yields (mostly 90-98%) in a short time (mostly 10-30 min), including a substrate for synthesizing the monomer of nylon-12 and a complicated steroidal substrate on a preparative scale. This research not only unveils for the first time the synthetic potential of substoichiometric amounts of dichloroimidazolidinediones in promoting chemical transformation but also offers yet another important illustration of the self-propagating cycle in the context of the Beckmann rearrangement activated by a structurally novel organic promoter.
Studies on non-thiazolidinedione antidiabetic Agents. 2. Novel oxyiminoalkanoic acid derivatives as potent glucose and lipid lowering agents
Imoto, Hiroshi,Sugiyama, Yasuo,Kimura, Hiroyuki,Momose, Yu
, p. 138 - 151 (2007/10/03)
We previously reported that (Z)-2-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl) methoxy]benzyloxyimino}-2-(4-phenoxyphenyl)acetic acid (3) showed potent glucose and lipid lowering effects in genetically obese and diabetic mice, KKA y. This compound a
