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

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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 Sept 2020
DOIs	https://doi.org/10.1016/j.tetlet.2020.152483
Publication status	Published - 5 Nov 2020

Keywords

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

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10.1016/j.tetlet.2020.152483

Patterson-etal-TH-2020-An-azide-and-acetylene-free-synthesis-of-1-substituted-1-2-3-triazolesAccepted author manuscript, 276 KBLicence: CC BY-NC-ND 4.0

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",

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AU - Patterson, Sarah J.M.

AU - Clark, Peter R.

AU - Williams, Glynn D.

AU - Tomkinson, Nicholas C.O.

PY - 2020/11/5

Y1 - 2020/11/5

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

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DO - 10.1016/j.tetlet.2020.152483

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SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

M1 - 152483

ER -

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

Abstract

Keywords

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

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

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

Cite this