N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
Publication type: Journal Article
Publication date: 2018-08-01
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30067041
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2 H-indazole synthesis, its reactivity was modulated for indazolone formation.
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Metrics
32
Total citations:
32
Citations from 2024:
7
(21.88%)
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GOST
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Zhu J. S. et al. N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights // Organic Letters. 2018. Vol. 20. No. 16. pp. 4736-4739.
GOST all authors (up to 50)
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Zhu J. S., Kraemer N., Shatskikh M. E., Li C. J., Son J., Haddadin M., Tantillo D. J., Kurth M. J. N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights // Organic Letters. 2018. Vol. 20. No. 16. pp. 4736-4739.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b01655
UR - https://doi.org/10.1021/acs.orglett.8b01655
TI - N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
T2 - Organic Letters
AU - Zhu, Jie S
AU - Kraemer, Niklas
AU - Shatskikh, Marina E
AU - Li, Clarabella J
AU - Son, Jung-Ho
AU - Haddadin, Makhluf
AU - Tantillo, Dean J.
AU - Kurth, Mark J.
PY - 2018
DA - 2018/08/01
PB - American Chemical Society (ACS)
SP - 4736-4739
IS - 16
VL - 20
PMID - 30067041
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Zhu,
author = {Jie S Zhu and Niklas Kraemer and Marina E Shatskikh and Clarabella J Li and Jung-Ho Son and Makhluf Haddadin and Dean J. Tantillo and Mark J. Kurth},
title = {N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.orglett.8b01655},
number = {16},
pages = {4736--4739},
doi = {10.1021/acs.orglett.8b01655}
}
Cite this
MLA
Copy
Zhu, Jie S., et al. “N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights.” Organic Letters, vol. 20, no. 16, Aug. 2018, pp. 4736-4739. https://doi.org/10.1021/acs.orglett.8b01655.