Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions
Publication type: Journal Article
Publication date: 1998-10-27
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
New guanidinylation reagents are reported. These reagents consist of N,N‘,N‘‘-tri-Boc-guanidine (1) and N,N‘,N‘‘-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,1 to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents2 N,N‘-di-Boc-N‘‘-triflylguanidine (3) and N,N‘-di-Cbz-N‘‘-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.
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148
Total citations:
148
Citations from 2024:
2
(1.36%)
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GOST
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Feichtinger K. et al. Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions // Journal of Organic Chemistry. 1998. Vol. 63. No. 23. pp. 8432-8439.
GOST all authors (up to 50)
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Feichtinger K., Sings H. L., Baker T. J., Matthews K., Goodman M. Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions // Journal of Organic Chemistry. 1998. Vol. 63. No. 23. pp. 8432-8439.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo9814344
UR - https://doi.org/10.1021/jo9814344
TI - Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions
T2 - Journal of Organic Chemistry
AU - Feichtinger, Konrad
AU - Sings, Heather L.
AU - Baker, Tracy J
AU - Matthews, Kenneth
AU - Goodman, Murray
PY - 1998
DA - 1998/10/27
PB - American Chemical Society (ACS)
SP - 8432-8439
IS - 23
VL - 63
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{1998_Feichtinger,
author = {Konrad Feichtinger and Heather L. Sings and Tracy J Baker and Kenneth Matthews and Murray Goodman},
title = {Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions},
journal = {Journal of Organic Chemistry},
year = {1998},
volume = {63},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/jo9814344},
number = {23},
pages = {8432--8439},
doi = {10.1021/jo9814344}
}
Cite this
MLA
Copy
Feichtinger, Konrad, et al. “Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions.” Journal of Organic Chemistry, vol. 63, no. 23, Oct. 1998, pp. 8432-8439. https://doi.org/10.1021/jo9814344.