An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles

Sarah J.M. Patterson; Peter R. Clark; Glynn D. Williams; Nicholas C.O. Tomkinson

doi:10.1016/j.tetlet.2020.152483

An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles

Sarah J.M. Patterson, Peter R. Clark, Glynn D. Williams, Nicholas C.O. Tomkinson

Pure And Applied Chemistry

Research output: Contribution to journal › Article

Abstract

This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excel- lent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines

Original language	English
Article number	152483
Journal	Tetrahedron Letters
Volume	61
Issue number	45
Early online date	28 Sep 2020
DOIs	https://doi.org/10.1016/j.tetlet.2020.152483
Publication status	E-pub ahead of print - 28 Sep 2020

Keywords

1,2,3-TriazoleDimethoxyacetaldehyde
Tosyl hydrazide
heterocyclisation
azide-free
acetylene-free

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10.1016/j.tetlet.2020.152483

https://www.sciencedirect.com/journal/tetrahedron-letters

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Patterson-etal-TH-2020-An-azide-and-acetylene-free-synthesis-of-1-substituted-1-2-3-triazoles
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Licence: CC BY-NC-ND 4.0
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1 Active

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation
Kerr, W., Brown, C., Florence, A., Jamieson, C., Johnston, B., Murphy, J., Palmer, D. & Tomkinson, N.
EPSRC (Engineering and Physical Sciences Research Council)
1/01/19 → 31/12/23
Project: Research

Cite this

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title = "An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles",

abstract = "This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excel- lent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines",

keywords = "1,2,3-TriazoleDimethoxyacetaldehyde, Tosyl hydrazide, heterocyclisation, azide-free, acetylene-free",

author = "Patterson, {Sarah J.M.} and Clark, {Peter R.} and Williams, {Glynn D.} and Tomkinson, {Nicholas C.O.}",

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AU - Patterson, Sarah J.M.

AU - Clark, Peter R.

AU - Williams, Glynn D.

AU - Tomkinson, Nicholas C.O.

PY - 2020/9/28

Y1 - 2020/9/28

N2 - This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excel- lent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines

AB - This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excel- lent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines

KW - 1,2,3-TriazoleDimethoxyacetaldehyde

KW - Tosyl hydrazide

KW - heterocyclisation

KW - azide-free

KW - acetylene-free

UR - https://www.sciencedirect.com/journal/tetrahedron-letters

U2 - 10.1016/j.tetlet.2020.152483

DO - 10.1016/j.tetlet.2020.152483

M3 - Article

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

M1 - 152483

ER -

An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles

Abstract

Keywords

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Embargoed Document

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

Cite this