Helvetica Chimica Acta p. 825 - 837 (1989)
Update date:2022-07-31
Topics:
Bozhkova, Nina
Heimgartner, Heinz
4-Alkoxy-1,3-oxazol-5(2H)-ones of type 4 and 7 were synthesized by two different methods: oxidation of the 4-(phenylthio)-1,3-oxazol-5(2H)-one 2a with m-chloroperbenzoic acid in the presence of an alcohol gave the corresponding 4-alkoxy derivatives 4, presumably via nucleophilic substitution of an intermediate sulfoxide (Scheme 2).The second approach is the BF3-catalyzed condensation of imino-acetates of type 6 and ketones (Scheme 3).The yields of this more straightforward method were modest due to the competitive formation of 1,3,5-triazine tricarboxylate 8.At 155 deg C, 1,3-oxazol-5(2H)-one 7b underwent decarboxylation leading to an alkoxy-substituted nitrile ylide which was trapped in a 1,3-dipolar cycloaddition by trifluoro-acetophenone to give the dihydro-oxazoles cis- and trans-9 (Scheme 4).In the absence of a dipolarophile, 1,5-dipolar cyclization of the intermediate nitrile ylide yielded isoindole derivatives 10 (Schemes 4 and 5).
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(1990)Doi:10.1039/c0ob00004c
(2010)Doi:10.1039/c0ob00201a
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(1989)Doi:10.1016/j.tet.2010.06.062
(2010)