Royal Society of Chemistry (RSC)
Organic and Biomolecular Chemistry
,  volume 18 ,  issue 26 ,  pages 4941-4945

[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold

Benjamin Zonker 1, 2, 3, 4, 5, 6
, 
Ediz Duman 1, 2, 3, 4, 5, 6
, 
Heike Hausmann 1, 2, 3, 4, 5, 6
, 
Jonathan D. Becker 7
, 
Jonathan Becker 3, 4, 5, 6, 8
, 
Radim Hrdina 1, 2, 3, 4, 5, 6
1
 
2
 
Institute of Organic Chemistry
3
 
4
 
Heinrich-Buff-Ring 17
5
 
35392 Giessen
6
 
GERMANY | 
7
 
8
 
Institute of Inorganic and Analytical Chemistry
Publication type: Journal Article
Publication date: 2020-06-22
Royal Society of Chemistry (RSC)
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
DOI:  10.1039/d0ob01156h
PubMed ID:  32583843
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We describe a Brønsted acid-catalysed cascade reaction consisting of a Wagner–Meerwein rearrangement and a subsequent intra- or intermolecular Friedel–Crafts reaction leading to adamantane-based heterocycles. In contrast to the reported W.–M. rearrangements, in this case an iminium moiety serves as the acceptor of a migrating nucleophilic alkyl group in a [1,2]-alkyl shift.
Found 
Found 
1 citation
Beloglazkina Elena
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N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
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Gorbunova Yuliya
DSc in Chemistry, professor, full member of the Russian Academy of Sciences 
284 publications,  4 398 citations,  65 reviews
h-index: 34
Lomonosov Moscow State University
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Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
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Research interests
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Lanthanides
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1 citation
Volcho Konstantin
DSc in Chemistry, professor of the Russian Academy of Sciences 
279 publications,  3 898 citations,  65 reviews
h-index: 31
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
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Danilkina Natalia
44 publications,  625 citations
h-index: 14
Saint Petersburg State University
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Research interests
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Heterocyclic compounds
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138 publications,  2 739 citations,  3 reviews
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A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
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Gazizov Almir
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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
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Research interests
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Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 599 citations
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A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
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Research interests
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Biological activity
Heterocyclic compounds
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Selenoamides
Thioamides
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Zagidullin Almaz
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Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
Organophosphorus chemistry
Synthesis of chiral phosphorus-containing ligands
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Aksenov Aleksandr
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Research interests
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Organic electrochemistry
Organic synthesis
Photochemistry
Plant protection
1 citation
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Mendeleev University of Chemical Technology of Russia
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Gause Institute of New Antibiotics
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GOST Copy
Zonker B. et al. [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 26. pp. 4941-4945.
GOST all authors (up to 50) Copy
Zonker B., Duman E., Hausmann H., Becker J. D., Becker J., Hrdina R. [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold // Organic and Biomolecular Chemistry. 2020. Vol. 18. No. 26. pp. 4941-4945.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1039/d0ob01156h
UR - https://xlink.rsc.org/?DOI=D0OB01156H
TI - [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold
T2 - Organic and Biomolecular Chemistry
AU - Zonker, Benjamin
AU - Duman, Ediz
AU - Hausmann, Heike
AU - Becker, Jonathan D.
AU - Becker, Jonathan
AU - Hrdina, Radim
PY - 2020
DA - 2020/06/22
PB - Royal Society of Chemistry (RSC)
SP - 4941-4945
IS - 26
VL - 18
PMID - 32583843
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Zonker,
author = {Benjamin Zonker and Ediz Duman and Heike Hausmann and Jonathan D. Becker and Jonathan Becker and Radim Hrdina},
title = {[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold},
journal = {Organic and Biomolecular Chemistry},
year = {2020},
volume = {18},
publisher = {Royal Society of Chemistry (RSC)},
month = {jun},
url = {https://xlink.rsc.org/?DOI=D0OB01156H},
number = {26},
pages = {4941--4945},
doi = {10.1039/d0ob01156h}
}
MLA
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MLA Copy
Zonker, Benjamin, et al. “[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold.” Organic and Biomolecular Chemistry, vol. 18, no. 26, Jun. 2020, pp. 4941-4945. https://xlink.rsc.org/?DOI=D0OB01156H.