62348-24-7Relevant articles and documents
Method for synthesizing furanosteroids
-
Page/Page column 8, (2009/06/27)
The present invention is a method for synthesizing furanosteroids. The method involves intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization of a functionalized alkyne oxazole to produce a furo[2,3-b]phenol derivative which is elaborated by intermolecular and intramolecular condensations to generate ring-A of the furanosteroid. Furanosteroids and pharmaceutical compositions containing the same are also provided.
Oxazole to Pyrimidine Ring Transformation: Synthesis of Potential Pyridoxine Antagonists
Sen, A. K.,Sengupta, D. K.
, p. 535 - 538 (2007/10/02)
The reaction of 4-methyloxazole-5-carbonyl chloride (I) with diazomethane gives 5-diazoacetyl-4-methyloxazole (II).Decomposition of II in methanol containing BF3-etherate provides the α-keto ether, 5-(methoxyacetyl)-4-methyloxazole (III).The α-ketol 5-(hydroxyacetyl)-4-methyloxazole (IV), obtained by decomposition of II in aq. acid, on treatment with dihydropyran in the presence of pyridinium toluene-p-sulfonate furnishes 4-methyl-5-oxazole (V).Warming III and V in methanolic ammonia in a sealed tube provides 5-hydroxy-4-methoxymethyl-6-methylpyrimidine (VI) and 5-hydroxy-6-methyl-4pyrimidine (VII), respectively.Acid-catalysed removal of the tetrahydropyranyl moiety from VII affords 5-hydroxy-4-hydroxymethyl-6-methylpyrimidine (VIII).