Oxaenediynes through the Nicholas-Type Macrocyclization Approach
Publication type: Journal Article
Publication date: 2016-10-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The Nicholas-type macrocyclization has been used for the first time for the synthesis of 10- and 11-membered oxaenediynes fused to a benzothiophene. The acyclic starting materials were easily synthesized by electrophilic cyclization of o-(buta-1,3-diynyl)thioanisoles followed by a Sonogashira coupling of the resulting 2-ethynyl-3-iodobenzothiophenes with functionalized alkynes. A high reactivity of the 10-membered oxacycles in the Bergman cyclization was predicted by DFT calculations and confirmed by differential scanning calorimetry. The ability of enediynes to induce single-strand PM2 DNA scissions was also found.
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Total citations:
19
Citations from 2024:
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(26.31%)
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MLA
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GOST
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Lyapunova A. G. et al. Oxaenediynes through the Nicholas-Type Macrocyclization Approach // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 28. pp. 4842-4851.
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Lyapunova A. G., Danilkina N. A., Khlebnikov A. F., Köberle B., Bräse S., Balova I. A. Oxaenediynes through the Nicholas-Type Macrocyclization Approach // European Journal of Organic Chemistry. 2016. Vol. 2016. No. 28. pp. 4842-4851.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201600767
UR - https://doi.org/10.1002/ejoc.201600767
TI - Oxaenediynes through the Nicholas-Type Macrocyclization Approach
T2 - European Journal of Organic Chemistry
AU - Lyapunova, Anna G
AU - Danilkina, Natalia A
AU - Khlebnikov, Alexander F
AU - Köberle, Beate
AU - Bräse, Stefan
AU - Balova, Irina A.
PY - 2016
DA - 2016/10/01
PB - Wiley
SP - 4842-4851
IS - 28
VL - 2016
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Lyapunova,
author = {Anna G Lyapunova and Natalia A Danilkina and Alexander F Khlebnikov and Beate Köberle and Stefan Bräse and Irina A. Balova},
title = {Oxaenediynes through the Nicholas-Type Macrocyclization Approach},
journal = {European Journal of Organic Chemistry},
year = {2016},
volume = {2016},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/ejoc.201600767},
number = {28},
pages = {4842--4851},
doi = {10.1002/ejoc.201600767}
}
Cite this
MLA
Copy
Lyapunova, Anna G., et al. “Oxaenediynes through the Nicholas-Type Macrocyclization Approach.” European Journal of Organic Chemistry, vol. 2016, no. 28, Oct. 2016, pp. 4842-4851. https://doi.org/10.1002/ejoc.201600767.
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