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

^*Corresponding author for this work

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

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.

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 - 4 Dec 2015

Keywords

ONE-POT SYNTHESIS
ASYMMETRIC-SYNTHESIS
BIOLOGICAL EVALUATION
BETA-LACTAMS
ACID-DERIVATIVES
AGENTS
DESIGN
COMBRETASTATIN-A4
LACTONIZATION
PYRIDINES

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10.1021/acs.orglett.5b02997

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation
Woollins, J. D. (PI), Ashbrook, S. E. (CoI), Morris, R. E. (CoI) & Slawin, A. M. Z. (CoI)
EPSRC
1/01/13 → 31/03/13
Project: Standard

Data underpinning: Organocatalytic synthesis of fused bicyclic 2,3-dihydro-1,3,4-oxadiazoles through an intramolecular cascade cyclization
Fugard, A. J. (Creator), Thompson, B. K. (Creator), Slawin, A. M. Z. (Creator), Taylor, J. E. (Creator) & Smith, A. D. (Creator), University of St Andrews, 2016
DOI: 10.17630/9c704848-8ca9-4e41-8811-2f2fea2e5f6c
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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, iPr(2)NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.",

keywords = "ONE-POT SYNTHESIS, ASYMMETRIC-SYNTHESIS, BIOLOGICAL EVALUATION, BETA-LACTAMS, ACID-DERIVATIVES, AGENTS, DESIGN, COMBRETASTATIN-A4, LACTONIZATION, PYRIDINES",

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

year = "2015",

month = dec,

day = "4",

doi = "10.1021/acs.orglett.5b02997",

language = "English",

volume = "17",

pages = "5824--5827",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "23",

}

TY - JOUR

T1 - Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

AU - Fugard, Alison J.

AU - Thompson, Bethany K.

AU - Slawin, Alexandra M. Z.

AU - Taylor, James E.

AU - Smith, Andrew D.

PY - 2015/12/4

Y1 - 2015/12/4

N2 - 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.

AB - 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.

KW - ONE-POT SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - BIOLOGICAL EVALUATION

KW - BETA-LACTAMS

KW - ACID-DERIVATIVES

KW - AGENTS

KW - DESIGN

KW - COMBRETASTATIN-A4

KW - LACTONIZATION

KW - PYRIDINES

U2 - 10.1021/acs.orglett.5b02997

DO - 10.1021/acs.orglett.5b02997

M3 - Article

SN - 1523-7060

VL - 17

SP - 5824

EP - 5827

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

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

Abstract

Keywords

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Datasets

Data underpinning: Organocatalytic synthesis of fused bicyclic 2,3-dihydro-1,3,4-oxadiazoles through an intramolecular cascade cyclization

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