41245-70-9Relevant academic research and scientific papers
Quinone C-H Alkylations via Oxidative Radical Processes
Hamsath, Akil,Galloway, Jordan D.,Baxter, Ryan D.
supporting information, p. 2915 - 2923 (2018/06/12)
A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.
Simple and effective route for synthesis of parvaquone, an antiprotozoal drug
Patil, Pravin C.,Akamanchi, Krishnacharya G.
, p. 58214 - 58216 (2015/02/19)
Parvaquone, an antiprotozoal agent against Theileria parva, was synthesized in 33.8% overall yield by using cheap, commercially available raw materials. A key intermediate, 2-cyclohexyl-1-naphthol, was synthesized in 86% yield by cyclohexylation of 1-naphthol and further converted into parvaquone in good yield through reaction sequences such as oxidation and epoxidation followed by isomerization.
Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation
Harrity, Joseph P. A.,Kerr, William J.,Middlemiss, David,Scott, James S.
, p. 219 - 227 (2007/10/03)
During attempts to synthesise the 2-hydroxy-1,4-naphthoquinone, parvaquone, 1, a novel chromium-mediated method for the synthesis of functionalised β-lactones from propargyl alcohols has been discovered. Additionally, using both dry state and ultrasound conditions, the total synthesis of parvaquone (1) has been achieved; the most efficient techniques deliver this target compound in up to 46% overall yield over, as low as, two synthetic processes.
ASYMMETRIC WEITZ - SCHEFFER EPOXIDATION PROMOTED BY BOVINE SERUM ALBUMIN. PART III. HIGHLY STEREOELECTIVE SYNTHESIS OF OPTICALLY ACTIVE EPOXYNAPHTHOQUINONES.
Colonna, Stefano,Gaggero, Nicoletta,Manfredi, Amedea,Spadoni, Massimo,Casella, Luigi,et al.
, p. 5169 - 5178 (2007/10/02)
The epoxidation of 2-substituted naphthoquinones with t-BuOOH in an aqueous buffer solution containing a small amount (up to 5 percent molar equiv) of bovine serum albumin (BSA) gives the corresponding epoxides with enantiomeric excess (e.e.) up to 100 pe
