Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family.
Publication type: Journal Article
Publication date: 2020-06-09
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32515592
Organic Chemistry
Abstract
A total synthesis of the Vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure Vasici-none, Rutaecarpine, Isaindigotone, and Luotonine were synthesized from readily available starting materials like hydroxy-proline, nitrobenzaldehyde, pyrrolidine, and piperidine in two-four operational steps without chromatography. The anti-fungal activity of all products was tested.
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31
Total citations:
31
Citations from 2024:
9
(29%)
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GOST
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Afanasyev O. I. et al. Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family. // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9347-9360.
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Afanasyev O. I., Podyacheva E., Rudenko A., Tsygankov A. A., Makarova M., Chusov D. Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family. // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9347-9360.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.0c00794
UR - https://doi.org/10.1021/acs.joc.0c00794
TI - Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family.
T2 - Journal of Organic Chemistry
AU - Afanasyev, Oleg I
AU - Podyacheva, Evgeniya
AU - Rudenko, Alexander
AU - Tsygankov, Alexey A.
AU - Makarova, Maria
AU - Chusov, Denis
PY - 2020
DA - 2020/06/09
PB - American Chemical Society (ACS)
SP - 9347-9360
IS - 14
VL - 85
PMID - 32515592
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Afanasyev,
author = {Oleg I Afanasyev and Evgeniya Podyacheva and Alexander Rudenko and Alexey A. Tsygankov and Maria Makarova and Denis Chusov},
title = {Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family.},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.0c00794},
number = {14},
pages = {9347--9360},
doi = {10.1021/acs.joc.0c00794}
}
Cite this
MLA
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Afanasyev, Oleg I., et al. “Redox condensations of o-nitrobenzaldehydes with amines under mild conditions - total synthesis of the Vasicinone family..” Journal of Organic Chemistry, vol. 85, no. 14, Jun. 2020, pp. 9347-9360. https://doi.org/10.1021/acs.joc.0c00794.