A two-stage iterative process for the synthesis of poly-oxazoles.
[reaction: see text]. Methodology has been developed to prepare bis-oxazoles via a two-stage iterative process. The sequence begins with C(2)-chlorination of a lithiated oxazole using hexachloroethane. Generation of the C(2)-C(4)(') bond by S(N)Ar substitution with TosMIC anion, followed by conversion to the heterocycle in a one-pot reaction with glyoxylic acid monohydrate, affords the desired bis-oxazole in good yield and purity. The two-stage process allows for efficient synthesis of a tris-oxazole and the first iterative preparation of a tetra-oxazole.
Atkins
Jeffery M
JM
Department of Chemistry, University of Michigan, Ann Arbor, 48109, USA.
Vedejs
Edwin
E
D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry
D010080:Oxazoles; D011108:Polymers; C431888:telomestatin