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

Chemistry of Materials and Catalysis

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

8 Citations (Scopus)

24 Downloads (Pure)

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-triazole
debenzylation
microwave
disubstituted
rearrangement

Access to Document

10.1055/s-0035-1562603

Accepted manuscriptAccepted author manuscript, 1.06 MB

Cite this

@article{41aa9b3cc681492ca67147646472cff2,

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 {\textquoteleft}click{\textquoteright} 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-triazole, debenzylation, microwave, disubstituted, rearrangement",

author = "{Bulman Page}, {Philip C.} 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",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "17",

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

AU - Bulman Page, Philip C.

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-triazole

KW - debenzylation

KW - microwave

KW - disubstituted

KW - rearrangement

U2 - 10.1055/s-0035-1562603

DO - 10.1055/s-0035-1562603

M3 - Article

VL - 27

SP - 2500

EP - 2504

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 17

ER -