Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group.
Olga Ivanova
1
,
Vladimir A Andronov
1
,
Vladimir S Vasin
2
,
Alexey N Shumsky
3
,
Igor V Trushkov
2, 4
Publication type: Journal Article
Publication date: 2018-12-05
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30517005
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Lewis-acid-induced domino transformations of donor-acceptor cyclopropanes, possessing a nucleophilic center embedded in a donor group, into functionalized 2,3-dihydrobenzo[ b]furans and 2,3-dihydrobenzo[ b]thiophenes are reported herein. An unusual switch of the electrophilic center in the three-membered ring, from the atom bearing a donor substituent to an unsubstituted carbon atom, was achieved by a judicious choice of Lewis acid, which induces the isomerization of a cyclopropane to an electrophilic alkene, and the length of linker, connecting a nucleophilic moiety and the small ring.
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Total citations:
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Citations from 2024:
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(22.22%)
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GOST
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Ivanova O. et al. Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group. // Organic Letters. 2018. Vol. 20. No. 24. pp. 7947-7952.
GOST all authors (up to 50)
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Ivanova O., Andronov V. A., Vasin V. S., Shumsky A. N., Rybakov V. B., Voskressensky L. G., Trushkov I. V. Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group. // Organic Letters. 2018. Vol. 20. No. 24. pp. 7947-7952.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b03491
UR - https://doi.org/10.1021/acs.orglett.8b03491
TI - Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group.
T2 - Organic Letters
AU - Ivanova, Olga
AU - Andronov, Vladimir A
AU - Vasin, Vladimir S
AU - Shumsky, Alexey N
AU - Rybakov, Victor B.
AU - Voskressensky, Leonid G.
AU - Trushkov, Igor V
PY - 2018
DA - 2018/12/05
PB - American Chemical Society (ACS)
SP - 7947-7952
IS - 24
VL - 20
PMID - 30517005
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
Copy
@article{2018_Ivanova,
author = {Olga Ivanova and Vladimir A Andronov and Vladimir S Vasin and Alexey N Shumsky and Victor B. Rybakov and Leonid G. Voskressensky and Igor V Trushkov},
title = {Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group.},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.8b03491},
number = {24},
pages = {7947--7952},
doi = {10.1021/acs.orglett.8b03491}
}
Cite this
MLA
Copy
Ivanova, Olga, et al. “Expanding the Reactivity of Donor-Acceptor Cyclopropanes: Synthesis of Benzannulated Five-Membered Heterocycles via Intramolecular Attack of a Pendant Nucleophilic Group..” Organic Letters, vol. 20, no. 24, Dec. 2018, pp. 7947-7952. https://doi.org/10.1021/acs.orglett.8b03491.
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