99924-18-2Relevant articles and documents
Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl-Lithium Exchange-Trapping
Mueller, Louis G.,Chao, Allen,Alwedi, Embarek,Natrajan, Maanasa,Fleming, Fraser F.
, p. 1500 - 1503 (2021/03/08)
Oxazoles are rapidly assembled through a sequential deprotonation-condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl-lithium exchange-trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through a first-in-class sulfur-lithium exchange-electrophilic trapping sequence whose versatility is illustrated in the three-step synthesis of the bioactive natural product streptochlorin.
Metalation of 4-oxazolinyloxazole derivatives. A convenient route to 2,4-bifunctionalized oxazoles.
Couture, Axel,Grandclaudon, Pierre,Hoarau, Christophe,Cornet, Josephine,Henichart, Jean-Pierre,Houssin, Raymond
, p. 3601 - 3606 (2007/10/03)
The synthesis of an array of 5-phenyloxazole derivatives bearing a variety of hydroxyalkyl groups at the C-2 position of the heterocyclic nucleus and possessing a formyl or a carboxyl function at C-4 is reported. These bifunctionalized compounds have been efficiently prepared by addition of carbonylated electrophiles to the 2-lithio derivative of 5-phenyloxazole preliminarily equipped with an oxazoline unit at the 4-position of the oxazole nucleus. It is demonstrated that this protocol offers a double advantage since it suppresses the troublesome electrocyclic ring-opening reaction and allows access to the target compounds by simple chemical transformation of the oxazoline ring system.
Synthesis and hypolipidemic activities of 5-thienyl-4-oxazoleacetic acid derivatives
Moriya,Takabe,Maeda,Matsumoto,Takashima,Takeyama
, p. 333 - 341 (2007/10/02)
A series of 2,5-disubstituted 4-oxazoleacetic acid derivatives was synthesized and evaluated for hypolipidemic activity. Among them, those with a thienyl group at C-5 of the oxazole ring exerted highly potent hypolipidemic effects in rats. 2-(4-Fluorophen