Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution
Michał Achmatowicz
1
,
Oliver R Thiel
1
,
Gilles Gorins
1
,
Corinne Goldstein
1
,
Caroline Affouard
1
,
Randy Jensen
1
,
ROBERT D. LARSEN
1
1
Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320-1799
|
Publication type: Journal Article
Publication date: 2008-07-29
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
18661950
Organic Chemistry
Abstract
An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways under VNS conditions, one leading to an isoxazole and the other resulting in the formal cyclopropanation of an aromatic nitro compound.
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18
Total citations:
18
Citations from 2025:
1
(5.56%)
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GOST
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Achmatowicz M. et al. Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution // Journal of Organic Chemistry. 2008. Vol. 73. No. 17. pp. 6793-6799.
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Achmatowicz M., Thiel O. R., Gorins G., Goldstein C., Affouard C., Jensen R., LARSEN R. D. Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution // Journal of Organic Chemistry. 2008. Vol. 73. No. 17. pp. 6793-6799.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo801131z
UR - https://doi.org/10.1021/jo801131z
TI - Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution
T2 - Journal of Organic Chemistry
AU - Achmatowicz, Michał
AU - Thiel, Oliver R
AU - Gorins, Gilles
AU - Goldstein, Corinne
AU - Affouard, Caroline
AU - Jensen, Randy
AU - LARSEN, ROBERT D.
PY - 2008
DA - 2008/07/29
PB - American Chemical Society (ACS)
SP - 6793-6799
IS - 17
VL - 73
PMID - 18661950
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2008_Achmatowicz,
author = {Michał Achmatowicz and Oliver R Thiel and Gilles Gorins and Corinne Goldstein and Caroline Affouard and Randy Jensen and ROBERT D. LARSEN},
title = {Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution},
journal = {Journal of Organic Chemistry},
year = {2008},
volume = {73},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jo801131z},
number = {17},
pages = {6793--6799},
doi = {10.1021/jo801131z}
}
Cite this
MLA
Copy
Achmatowicz, Michał, et al. “Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution.” Journal of Organic Chemistry, vol. 73, no. 17, Jul. 2008, pp. 6793-6799. https://doi.org/10.1021/jo801131z.