General synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles

A general and mild synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles is presented. A wide variety of sensitive functional groups are tolerated and a one-pot procedure is also demonstrated. Tetrasubstituted alkenyl-1,3,4-oxadiazoles were synthesized in moderate to excellent yield, under mild co...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 4; pp. 511 - 514
Main Authors James, Clint A., Poirier, Brigitte, Grisé, Christiane, Martel, Alain, Ruediger, Edward H.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.01.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIACYLHYDRAZINES
REAGENT
ACID
HYDRAZIDES
HETEROCYCLES
1,2-DIACYLHYDRAZINES
1,3,4-OXADIAZOLES
CYCLIZATION
CHLORIDE
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Summary:A general and mild synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles is presented. A wide variety of sensitive functional groups are tolerated and a one-pot procedure is also demonstrated. Tetrasubstituted alkenyl-1,3,4-oxadiazoles were synthesized in moderate to excellent yield, under mild conditions and in the presence of sensitive functional groups, via the cyclization of diacylhydrazides using PPh 3 and hexachloroethane in the presence of Hünig’s base. An efficient one-pot acylation/cyclization approach for the conversion of acylhydrazides to 1,3,4-oxadiazoles is also described. The complexity of our substrate as well as the wide range of functional groups incorporated substantially broadens the scope of this methodology.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.11.057