Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3-ones

Mark A Graham; Paul A Bethel; Jonathan Burgess; Gary Fairley; Steve C Glossop; Ryan D R Greenwood; Clifford D Jones; Scott Lovell; Steve Swallow

doi:10.1021/ol402920z

Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3-ones

Mark A Graham, Paul A Bethel, Jonathan Burgess, Gary Fairley, Steve C Glossop, Ryan D R Greenwood, Clifford D Jones, Scott Lovell, Steve Swallow

Department of Life Sciences

AstraZeneca UK Ltd

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

5 Citations (SciVal)

Abstract

A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and alkyl functional groups are tolerated, providing a versatile route for the synthesis of triazolones.

Original language	English
Pages (from-to)	6078-81
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	23
Early online date	18 Nov 2013
DOIs	https://doi.org/10.1021/ol402920z
Publication status	Published - 6 Dec 2013

Keywords

Lithium/chemistry
Molecular Structure
Organometallic Compounds/chemistry
Triazoles/chemical synthesis

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10.1021/ol402920z

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title = "Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3-ones",

abstract = "A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and alkyl functional groups are tolerated, providing a versatile route for the synthesis of triazolones. ",

keywords = "Lithium/chemistry, Molecular Structure, Organometallic Compounds/chemistry, Triazoles/chemical synthesis",

author = "Graham, \{Mark A\} and Bethel, \{Paul A\} and Jonathan Burgess and Gary Fairley and Glossop, \{Steve C\} and Greenwood, \{Ryan D R\} and Jones, \{Clifford D\} and Scott Lovell and Steve Swallow",

year = "2013",

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doi = "10.1021/ol402920z",

language = "English",

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T1 - Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3-ones

AU - Graham, Mark A

AU - Bethel, Paul A

AU - Burgess, Jonathan

AU - Fairley, Gary

AU - Glossop, Steve C

AU - Greenwood, Ryan D R

AU - Jones, Clifford D

AU - Lovell, Scott

AU - Swallow, Steve

PY - 2013/12/6

Y1 - 2013/12/6

N2 - A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and alkyl functional groups are tolerated, providing a versatile route for the synthesis of triazolones.

AB - A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and alkyl functional groups are tolerated, providing a versatile route for the synthesis of triazolones.

KW - Lithium/chemistry

KW - Molecular Structure

KW - Organometallic Compounds/chemistry

KW - Triazoles/chemical synthesis

UR - https://www.scopus.com/pages/publications/84890098838

U2 - 10.1021/ol402920z

DO - 10.1021/ol402920z

M3 - Article

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EP - 6081

JO - Organic letters

JF - Organic letters

IS - 23

ER -

Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3-ones

Abstract

Keywords

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