20357-48-6Relevant academic research and scientific papers
Highly E-selective and effective synthesis of antiarthritic drug candidate S-2474 using quinone methide derivatives
Inagaki, Masanao,Haga, Nobuhiro,Kobayashi, Makoto,Ohta, Naoki,Kamata, Susumu,Tsuri, Tatsuo
, p. 125 - 128 (2002)
We have developed an efficient and E-selective synthesis of an antiarthritic drug candidate (E)-(5)-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-ethyl- 1,2-isothiazolidine-1,1-dioxide (S-2474; 1), in which α-methoxy-p-quinone methide is used as a key intermediate. α-Methoxy-p-quinone methide was revealed to be an equivalent to a p-hydroxy protected benzaldehyde. It reacts smoothly with α-sulfonyl carbanion to give 1,6-addition intermediates, which can be further processed to provide S-2474 directly in the presence of a base. This procedure gives S-2474 as an almost single isomer on the benzylidene double bond in excellent yield and thus is a very practical method adaptable to large-scale synthesis. The detailed mechanistic aspects are studied and discussed.
PROCESS FOR PREPARING SUBSTITUTED 1,4-QUINONE METHIDES
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Page/Page column 7, (2010/11/03)
A method for preparing a substituted 1,4-quinone methide from a 3,5-disubstituted 4-hydroxybenzaldehyde is provided. Also provided is a method to prepare a 3,5-disubstituted 4-hydroxybenzaldehyde from the corresponding 2,6-disubstituted phenol.
Oxidative Dehydrogenation of Sterically Hindered para-Substituted Phenols with 3,3′,5,5′-Tetra-tert-butyl-4,4′-diphenoquinone
Mukmeneva,Bukharov,Kadyrova,Zharkova,Gorshunova,Fazlieva
, p. 1486 - 1489 (2007/10/03)
The reactivity of 4-methyl-, 4-mercapto-, and 4-methoxymethyl-2,6-di-tert-butylphenols in oxidative dehydrogenation with 3,3′,5,5′-tetra-tert-butyl-4,4′-diphenoquinone was studied, and the structure of products was determined.
Method for producing benzylidene derivatives
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, (2008/06/13)
A selective and high-yield method is described for producing stereoisomeric benzylidene derivatives of the formula III: STR1 wherein R1 and R2 each independently is lower alkyl, lower alkoxy or halogen; Y is SO2, SO or CO;
