24752-66-7Relevant articles and documents
Atom-economic amide synthesis by using an iron-substituted polyoxometalate catalyst
Shi, Da,Wang, Aiping,Wang, Jingjing,Xie, Ya,Yu, Han
supporting information, p. 1127 - 1130 (2022/02/03)
We report an efficient and economical amidation strategy by using a polyoxometalate-based iron catalyst that affords the corresponding amide products in good yields. All of the aliphatic, aromatic and heterocyclic substrates are produced in high yields without additional base or organic ligands. Most importantly, the first example of heterogeneous iron(iii)-catalyzed formation of the diamides is developed.
Regioselective Thermal [3+2]-Dipolar Cycloadditions of α-Diazoacetates with α-Sulfenyl/Sulfinyl/Sulfonyl-β-Chloroacrylamide Derivatives to Form Densely Functionalised Pyrazoles
Flynn, Aaran J.,Ford, Alan,Khandavilli, U. B. Rao,Lawrence, Simon E.,Maguire, Anita R.
supporting information, p. 5368 - 5384 (2019/06/24)
Highly regioselective synthetic methodology leading to densely functionalised C(3), C(4) and C(5) substituted pyrazoles 10a–q, 14a-i and 16a–g via thermal [3+2]-dipolar cycloaddition, of α-diazoacetates and α-thio-β-chloroacrylamides, at the sulfide, sulfoxide and sulfone levels of oxidation, is described. This method allows access to C(4)-sulfenyl or sulfonyl pyrazoles, through migration of the sulfur substituent at the sulfide and sulfone oxidation levels, while elimination of the sulfinyl group leading to 3,5-disubstituted pyrazoles, is observed. While the sulfide migration is readily rationalised, the carbon to carbon 1,2-sulfonyl migration is unprecedented and mechanistically intriguing. The synthetically versatile generation of densely functionalised pyrazoles containing substituents amenable to further modification offers advantages over alternative synthetic routes. Isolation of the N-alkylated pyrazoles 11a and 12a as by-products from the cycloaddition through further reaction of the pyrazoles 10 with excess α-diazoacetate, proved useful in rationalising the tautomeric behaviour evident in the NMR spectra of the pyrazoles, with the position of tautomeric equilibrium influenced by solvent and substituents.
Design, synthesis and biological evaluation of novel dicarbonylalkyl piperazine derivatives as neuroprotective agents
Wang, Wen-Ya,Shen, Cheng-Wu,Weng, Zhi-Jie,Wang, Tie-Chuang,Zhang, Chuang,Jin, Xun-Qi,Li, Jian-Qi
supporting information, p. 387 - 390 (2016/03/16)
In the search of novel neuroprotective agents with higher potency than our previously identified anti-ischemic stroke drug candidate 1, a series of novel dicarbonyl piperazine derivatives were synthesized and evaluated on their neuroprotective activity via oxygen-glucose deprivation test in the neuron-like PC12 cells, hypoxia tolerance model in mice and focal cerebral ischemia model in rats. The result obtained indicated that compounds 7f, 7k and 7o, exhibited neuroprotective activity. Particularly, compound 7o containing 2,5-dimethylpiperazin moiety, showed prolonged life time of mice and reduced cerebral infarction of rats, which provided a potential candidate for the development of neuroprotective agents.
