1226-26-2Relevant articles and documents
THERMODYNAMICS OF PHENYL GLYCIDYL ETHER AND ITS REACTIONS WITH DIPHENYLCARBODIIMIDE AND PHENYL ISOCYANATE WITH THE FORMATION OF IMINOOXAZOLIDINE AND OXAZOLIDINONE IN THE 0-330 K RANGE
Lebedev, B. V.,Bykova, T. A.,Kiparisova, E. G.,Frenkel', Ts. M.,Fainleib, A. M.,Pankratov, V. A.
, p. 1082 - 1086 (1988)
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REACTION OF DIPHENYLCARBODIIMIDE WITH PHENYL GLYCIDYL ETHER
Pankratov, V. A.,Frenkel, Ts. M.,Fainleib, A. M.,Vasil'ev, Yu. V.,Komarova, L. I.,et al.
, p. 431 - 433 (1983)
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Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones
Rostami, Ali,Ebrahimi, Amirhossein,Sakhaee, Nader,Golmohammadi, Farhad,Al-Harrasi, Ahmed
, p. 40 - 55 (2021/10/20)
An electrostatically enhanced phenol is utilized as a straightforward, sustainable, and potent one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20-60 min). A careful assessment of the efficacy of various positively charged phenols and anilines and the impact of several factors, such as catalyst loading, temperature, and the kind of nucleophile, on catalytic reactivity were examined. Under neat conditions, this one-component catalytic platform was exploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substituted epoxides and isocyanates within minutes, where up to 96% yield and high degree of selectivity were attained. DFT calculations to achieve reaction barriers for different catalytic routes were conducted to provide mechanistic understanding and corroborated the experimental findings in which concurrent epoxide ring-opening and isocyanate incorporation were proposed.
Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones
Nishiyori, Ryuichi,Okuno, Ken,Shirakawa, Seiji
, p. 4937 - 4941 (2020/07/30)
Among the wide variety of heterocycles, 2-oxazolidinones are recognized as some of the most important heterocyclic compounds in medicinal chemistry. Therefore, the development of a practical method for their synthesis would be an important development. He
A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides
Zhou, Meixia,Zheng, Xizhou,Wang, Yaorong,Yuan, Dan,Yao, Yingming
, p. 5783 - 5787 (2019/04/14)
Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.
