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Synlett 1997; 1997(3): 283-284
DOI: 10.1055/s-1997-766
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Synthesis of 1,3,4-Oxadiazoles from Carboxylic Hydrazides and of 1,2-Oxazin-6-ones from α-(Hydroxyimino)carboxylic Esters with Keteneylidene Triphenylphosphorane

Jonas Löffler, Rainer Schobert*
  • *Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestraße 42, D-91054 Erlangen, Germany, Fax +49 9131 85 6864; E-mail schobert@organik.uni-erlangen.de
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Publikationsdatum:
31. Dezember 2000 (online)

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In a one-pot procedure 1,3,4-oxadiazoles 8 are prepared from carboxylic hydrazides 2 and keteneylidene triphenylphosphorane 1 via an untypical intermolecular Wittig olefination of a carbamate type carbonyl group. Under similar conditions, reaction of 1 and α-(hydroxyimino) carboxylic esters 9 furnishes 1,2-oxazin-6-ones 11 by a different process including an intramolecular olefination step.

1,3,4-oxadiazoles - 1,2-oxazines - phosphorus ylides - cascade reaction