NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups

Abstract

NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from

Original language	English
Article number	Y06505ST
Pages (from-to)	2847-2850
Number of pages	4
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-2005-918944
Publication status	Published - 3 Nov 2005
Externally published	Yes

Keywords

Alkynes
Azides
Click chemistry
Cycloaddition
Heterocycles
Protecting groups
Triazoles

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2005-918944

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title = "NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups",

abstract = "NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from ",

keywords = "Alkynes, Azides, Click chemistry, Cycloaddition, Heterocycles, Protecting groups, Triazoles",

author = "Loren, {Jon C.} and Antoni Krasi{\'n}ski and Fokin, {Valery V.} and Sharpless, {K. Barry}",

year = "2005",

month = nov,

day = "3",

doi = "10.1055/s-2005-918944",

language = "English",

pages = "2847--2850",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "18",

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T1 - NH-1,2,3-triazoles from azidomethyl pivalate and carbamates

T2 - Base-labile N-protecting groups

AU - Loren, Jon C.

AU - Krasiński, Antoni

AU - Fokin, Valery V.

AU - Sharpless, K. Barry

PY - 2005/11/3

Y1 - 2005/11/3

N2 - NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from

AB - NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from

KW - Alkynes

KW - Azides

KW - Click chemistry

KW - Cycloaddition

KW - Heterocycles

KW - Protecting groups

KW - Triazoles

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