The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1 ) is researched.Formula: C6H7NO3.Sagud, Ivana; Bozic, Simona; Marinic, Zeljko; Sindler-Kulyk, Marija published the article 《Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles》 about this compound( cas:118994-89-1 ) in Beilstein Journal of Organic Chemistry. Keywords: benzobicyclooctenone preparation; fused oxazoline benzobicyclooctadiene preparation ring opening; cis trans vinylstyryl oxazole preparation intramol photocycloaddition diastereoselective; bicyclo[3.2.1]octane; intramolecular photocycloaddition; oxazole; styryl; vinyl. Let’s learn more about this compound (cas:118994-89-1).
A new photochem. approach for the preparation of functionalized benzobicyclo[3.2.1]octenones was described via fused oxazoline derivatives prepared from 4- and 5-(2-vinylstyryl)oxazoles. Novel cis/trans 4- and 5-(2-vinylstyryl)oxazoles were synthesized by Wittig reactions of o-xylelenebis(triphenylphosphoniumbromide) and formaldehyde with 4- and 5-oxazolecarbaldehydes resp. Trans-5-(2-vinylstyryl)oxazole was also prepared by the van Leusen reaction of trans-3-(2-vinylphenyl)acrylaldehyde which was prepared from o-vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The photochem. intramol. cycloaddition of cis/trans isomers of 4- and 5-(2-vinylstyryl)oxazoles afforded diverse fused oxazoline-benzobicyclo[3.2.1]octadienes I [stereo = R or S] and II which were relatively unstable. These fused oxazoline-benzobicyclo[3.2.1]octadienes underwent oxazoline ring opening spontaneously or on silica gel followed by formation of benzobicyclo[3.2.1]octenone derivatives III [X = O, stereo = R or S; X = NH, stereo = S]. Small quantity of electrocyclization product 4-(1,2-Dihydronaphthalen-2-yl)oxazole was also isolated along with desired photocycloaddition products on irradiation of 4-(2-vinylstyryl)oxazole.
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