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

Base-labile N-protecting groups

Jon C. Loren, Antoni Krasiński, Valery V. Fokin, K. Barry Sharpless

Research output: Contribution to journalArticle

73 Citations (Scopus)

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 languageEnglish
Article numberY06505ST
Pages (from-to)2847-2850
Number of pages4
JournalSynlett
Issue number18
DOIs
Publication statusPublished - 3 Nov 2005
Externally publishedYes

Fingerprint

Triazoles
Carbamates
Azides
Sodium Hydroxide
Alkynes
Cycloaddition
Copper
morpholine

Keywords

  • Alkynes
  • Azides
  • Click chemistry
  • Cycloaddition
  • Heterocycles
  • Protecting groups
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Loren, J. C., Krasiński, A., Fokin, V. V., & Sharpless, K. B. (2005). NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups. Synlett, (18), 2847-2850. [Y06505ST]. https://doi.org/10.1055/s-2005-918944

NH-1,2,3-triazoles from azidomethyl pivalate and carbamates : Base-labile N-protecting groups. / Loren, Jon C.; Krasiński, Antoni; Fokin, Valery V.; Sharpless, K. Barry.

In: Synlett, No. 18, Y06505ST, 03.11.2005, p. 2847-2850.

Research output: Contribution to journalArticle

Loren, JC, Krasiński, A, Fokin, VV & Sharpless, KB 2005, 'NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups', Synlett, no. 18, Y06505ST, pp. 2847-2850. https://doi.org/10.1055/s-2005-918944
Loren, Jon C. ; Krasiński, Antoni ; Fokin, Valery V. ; Sharpless, K. Barry. / NH-1,2,3-triazoles from azidomethyl pivalate and carbamates : Base-labile N-protecting groups. In: Synlett. 2005 ; No. 18. pp. 2847-2850.
@article{b7f18634dd8b4a9680840d7efa4379d6,
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 Krasiński and Fokin, {Valery V.} and Sharpless, {K. Barry}",
year = "2005",
month = "11",
day = "3",
doi = "10.1055/s-2005-918944",
language = "English",
pages = "2847--2850",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "18",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=27844570848&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27844570848&partnerID=8YFLogxK

U2 - 10.1055/s-2005-918944

DO - 10.1055/s-2005-918944

M3 - Article

SP - 2847

EP - 2850

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 18

M1 - Y06505ST

ER -