19483-24-0Relevant articles and documents
Haloacetylated Enol Ethers. 8 [12]. Reaction of β-Alkoxyvinyl Trihalomethyl Ketones with Guanidine Hydrochloride. Synthesis of 4-Trihalomethyl-2-Aminopyrimidines
Zanatta, Nilo,Cortelini, Maria De F. M.,Carpes, Marcos J. S.,Bonacorso, Helio G.,Martins, Marcos A. P.
, p. 509 - 513 (1997)
In this work the results of the reaction of β-alkoxyvinyl trihalomethyl ketones 1, 2a-e, with guanidine hydrochloride are reported. Depending on the ketone 1 or 2 and the conditions under which the reactions were carried out, 4-trihalomethyl-2-amino pyrimidines, β-alkoxyvinyl carboxylic acids, or β-acetal carboxylic esters were obtained.
INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE
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Page/Page column 334, (2017/09/02)
The present disclosure is directed to compounds of formula I and methods of their use and preparation, as well as compositions comprising compounds of formula I.
Electroorganic Synthesis, 56. Synthesis of Advanced Prostaglandin Precursors by Kolbe Electrolysis, I. - Preparation of (1'R,4'S,3R/S)-3-(cis-4-Acetoxycyclopent-2-enyloxy)-3-ethoxypropionic Acid
Weiguny, Jens,Schaefer, Hans J.
, p. 225 - 234 (2007/10/02)
The key intermediate of a novel synthesis of prostaglandin precursors, (1'R,4'S,3R/S)-3-(cis-4-acetoxycyclopent-2-enyloxy)-3-ethoxypropionic acid (3), is prepared by two different synthetic sequences: In a first strategy transacetalization of ethyl 3,3-diethoxypropionate (6) with (1R,4S)-4-acetoxy-1-hydroxy-2-cyclopentene (7) leads to the formation of the mixed acetal 8.By subsequent hydrolysis and acylation 8 could be converted into acid 3 in six steps in 6percent overall yield.However, the generation of acid 3 by bromoalkoxidation of 3-ethoxyacrylates 13d, e and subsequent electrochemical reduction proved to be more efficient.In this reduction it is possible to debrominate the α-bromo esters 14d, e and to remove the 2-haloethyl ester group in one step.Using this reaction sequence, we could synthesize acid 3 in five steps in 38percent overall yield. - Key Words: Kolbe electrolysis / Radical cyclization / Electrochemical dehalogenation / Prostaglandins