Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate
Publication type: Journal Article
Publication date: 2018-02-12
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29431446
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Reaction options, alkoxide vs hydroxide vs amine addition to the key intermediate (o-nitrosoimine) generated in the Davis-Beirut reaction of an o-nitrobenzylamine substrate, are reported to explain the nucleophilic addition selectivity of this one-pot indazole-forming process. The hydroxide addition/deprotection pathway as well as the fate of the resulting o-nitrosobenzaldehyde were both uncovered with several o-nitrobenzylamine substrates, and design elements required for an efficient double Davis-Beirut reaction, inspired by new mechanistic insights, were defined.
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Total citations:
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Citations from 2024:
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Zhu J. S. et al. Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate // Organic Letters. 2018. Vol. 20. No. 5. pp. 1308-1311.
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Zhu J. S., Duong M. R., Teuthorn A. P., Lu Julia Y., Son J., Haddadin M., Kurth M. J. Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate // Organic Letters. 2018. Vol. 20. No. 5. pp. 1308-1311.
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TY - JOUR
DO - 10.1021/acs.orglett.8b00036
UR - https://doi.org/10.1021/acs.orglett.8b00036
TI - Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate
T2 - Organic Letters
AU - Zhu, Jie S
AU - Duong, Matthew R
AU - Teuthorn, Andrew P
AU - Lu Julia, Y.
AU - Son, Jung-Ho
AU - Haddadin, Makhluf
AU - Kurth, Mark J.
PY - 2018
DA - 2018/02/12
PB - American Chemical Society (ACS)
SP - 1308-1311
IS - 5
VL - 20
PMID - 29431446
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2018_Zhu,
author = {Jie S Zhu and Matthew R Duong and Andrew P Teuthorn and Y. Lu Julia and Jung-Ho Son and Makhluf Haddadin and Mark J. Kurth},
title = {Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.8b00036},
number = {5},
pages = {1308--1311},
doi = {10.1021/acs.orglett.8b00036}
}
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MLA
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Zhu, Jie S., et al. “Davis–Beirut Reaction: Alkoxide versus Hydroxide Addition to the Key o-Nitrosoimine Intermediate.” Organic Letters, vol. 20, no. 5, Feb. 2018, pp. 1308-1311. https://doi.org/10.1021/acs.orglett.8b00036.