Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles

Philip C. Bulman Page; G. Richard Stephenson; James Harvey; Alexandra M. Z. Slawin

doi:10.1055/s-0035-1562603

Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles

Philip C. Bulman Page, G. Richard Stephenson, James Harvey, Alexandra M. Z. Slawin

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

Abstract

A method that cleanly converts the 1,4-disubstituted 1,2,3-triazole products of the copper-catalyzed click' dipolar cycloaddition reaction of benzyl azide with terminal alkynes into 1,5-disubstituted triazoles is described. Selective N-alkylation of 1,4-disubstituted 1,2,3-triazoles under microwave irradiation is followed by debenzylation of the resulting 1,3,4-trisubstituted triazolium cations by treatment with potassium tert-butoxide.

Original language	English
Pages (from-to)	2500-2504
Number of pages	5
Journal	Synlett
Volume	27
Issue number	17
Early online date	1 Aug 2016
DOIs	https://doi.org/10.1055/s-0035-1562603
Publication status	Published - Oct 2016

Keywords

1,2,3-triazoles
Debenzylation
Microwave
Disubstituted
Rearrangement

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10.1055/s-0035-1562603

Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles (dataset)
Bulman Page, P. C. B. P. (Creator), Stephenson, G. R. (Creator), Harvey, J. (Creator) & Slawin, A. M. Z. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/ccdc.csd.cc1ln92m, https://dx.doi.org/10.5517/ccdc.csd.cc1ln92m
Dataset

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title = "Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles",

abstract = "A method that cleanly converts the 1,4-disubstituted 1,2,3-triazole products of the copper-catalyzed click' dipolar cycloaddition reaction of benzyl azide with terminal alkynes into 1,5-disubstituted triazoles is described. Selective N-alkylation of 1,4-disubstituted 1,2,3-triazoles under microwave irradiation is followed by debenzylation of the resulting 1,3,4-trisubstituted triazolium cations by treatment with potassium tert-butoxide.",

keywords = "1,2,3-triazoles, Debenzylation, Microwave, Disubstituted, Rearrangement",

author = "Page, {Philip C. Bulman} and Stephenson, {G. Richard} and James Harvey and Slawin, {Alexandra M. Z.}",

year = "2016",

month = oct,

doi = "10.1055/s-0035-1562603",

language = "English",

volume = "27",

pages = "2500--2504",

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T1 - Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles

AU - Page, Philip C. Bulman

AU - Stephenson, G. Richard

AU - Harvey, James

AU - Slawin, Alexandra M. Z.

PY - 2016/10

Y1 - 2016/10

N2 - A method that cleanly converts the 1,4-disubstituted 1,2,3-triazole products of the copper-catalyzed click' dipolar cycloaddition reaction of benzyl azide with terminal alkynes into 1,5-disubstituted triazoles is described. Selective N-alkylation of 1,4-disubstituted 1,2,3-triazoles under microwave irradiation is followed by debenzylation of the resulting 1,3,4-trisubstituted triazolium cations by treatment with potassium tert-butoxide.

AB - A method that cleanly converts the 1,4-disubstituted 1,2,3-triazole products of the copper-catalyzed click' dipolar cycloaddition reaction of benzyl azide with terminal alkynes into 1,5-disubstituted triazoles is described. Selective N-alkylation of 1,4-disubstituted 1,2,3-triazoles under microwave irradiation is followed by debenzylation of the resulting 1,3,4-trisubstituted triazolium cations by treatment with potassium tert-butoxide.

KW - 1,2,3-triazoles

KW - Debenzylation

KW - Microwave

KW - Disubstituted

KW - Rearrangement

U2 - 10.1055/s-0035-1562603

DO - 10.1055/s-0035-1562603

M3 - Article

SN - 0936-5214

VL - 27

SP - 2500

EP - 2504

JO - Synlett

JF - Synlett

IS - 17

ER -

Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles

Abstract

Keywords

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Ruthenium-free preparation of 1,5-disubstituted triazoles by alkylative debenzylation of 1,4-disubstituted triazoles (dataset)

Cite this