866784-78-3Relevant academic research and scientific papers
The first example of a diastereoselective thio-Ugi reaction: A new synthetic approach to chiral imidazole derivatives
Gulevich, Anton V.,Balenkova, Elizabeth S.,Nenajdenko, Valentine G.
, p. 7878 - 7885 (2008/03/11)
(Chemical Equation Presented) The first example of a diastereoselective thio-Ugi reaction with chiral α-methylbenzylamine is described. The reaction results in formation of two diastereomers of thioamides, the major of which was isolated. We have found that under similar conditions stereochemical results of the thio-Ugi reaction are opposite to stereochemical results of the Ugi reaction. Several chiral thioamides were synthesized. The reaction of thioamides with ammonia results in substituted amidines, which can be cyclized to imidazole derivatives in aqueous HCl. The synthesis of chiral imidazole derivatives was elaborated. Using certain approaches, both isomers of a key synthon in the synthesis of SB203386 (an orally bioactive HIV-1 protease inhibitor) were prepared. The scope, limitations, and stereochemistry of the approach are discussed.
A straightforward approach towards thiazoles and endothiopeptides via Ugi reaction
Kazmaier, Uli,Ackermann, Stefanie
, p. 3184 - 3187 (2007/10/03)
Endothiopeptides can easily be obtained via Ugi reaction using thio acids as acid components. If isonitriles with an acetal group are applied, the endothiopeptides can directly be converted into thiazoles using TMSCl-NaI under microwave irradiation. The Royal Society of Chemistry 2005.
