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

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

Department of Chemistry

University of St Andrews

Research output: Contribution to journal › Article › peer-review

22 Citations (SciVal)

Abstract

Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr₂NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

Original language	English
Pages (from-to)	5824-5827
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.5b02997
Publication status	Published - 24 Nov 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5b02997

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

abstract = "Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr2NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.",

author = "Fugard, {Alison J.} and Thompson, {Bethany K.} and Slawin, {Alexandra M.Z.} and Taylor, {James E.} and Smith, {Andrew D.}",

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AU - Fugard, Alison J.

AU - Thompson, Bethany K.

AU - Slawin, Alexandra M.Z.

AU - Taylor, James E.

AU - Smith, Andrew D.

PY - 2015/11/24

Y1 - 2015/11/24

N2 - Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr2NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

AB - Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr2NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

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U2 - 10.1021/acs.orglett.5b02997

DO - 10.1021/acs.orglett.5b02997

M3 - Article

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SN - 1523-7060

VL - 17

SP - 5824

EP - 5827

JO - Organic Letters

JF - Organic Letters

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ER -

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

Abstract

ASJC Scopus subject areas

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