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 | |
| Publication status | Published - 3 Nov 2005 |
| Externally published | Yes |
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Keywords
- Alkynes
- Azides
- Click chemistry
- Cycloaddition
- Heterocycles
- Protecting groups
- Triazoles
ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
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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 -