Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

Alison J Fugard; Bethany K Thompson; Alexandra M Z Slawin; James E Taylor; Andrew D Smith

doi:10.1021/acs.orglett.5b02997

Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

Org Lett. 2015 Dec 4;17(23):5824-7. doi: 10.1021/acs.orglett.5b02997. Epub 2015 Nov 24.

Authors

Alison J Fugard¹, Bethany K Thompson¹, Alexandra M Z Slawin¹, James E Taylor¹, Andrew D Smith¹

Affiliation

¹ EaStCHEM, School of Chemistry, University of St. Andrews , North Haugh, St. Andrews, KY16 9ST, U.K.

PMID: 26598296
DOI: 10.1021/acs.orglett.5b02997

Abstract

Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr(2)NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

Publication types

Research Support, Non-U.S. Gov't

Grants and funding

279850/ERC_/European Research Council/International