Advanced Synthesis and Catalysis, volume 353, issue 7, pages 1125-1134
Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene
Olga Ivanova
1, 2
,
Ekaterina M Budynina
3, 4
,
Alexey O Chagarovskiy
1, 2
,
Alexey E Kaplun
1, 2
,
Igor V Trushkov
3, 4
,
Mikhail Y. Melnikov
1, 2
1
M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russia, Fax: (+7)-495-939-1814
|
2
phone: (+7)-495-939-1316
3
M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russia, Fax: (+7)‐495‐939‐1814
|
4
phone: (+7)‐495‐939‐1316
Publication type: Journal Article
Publication date: 2011-05-03
Journal:
Advanced Synthesis and Catalysis
Q1
Q1
SJR: 1.020
CiteScore: 9.4
Impact factor: 4.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
A novel Lewis acid-catalyzed [3+4] annulation of 2-(heteroaryl)cyclopropane-1,1-dicarboxylates with cyclopentadiene is reported. This reaction proceeds via an electrophilic attack of the Lewis acid-activated donor-acceptor cyclopropane onto cyclopentadiene followed by Friedel–Crafts intramolecular alkylation of the heteroarene substituent. This is the first general example of reactions of donor-acceptor cyclopropanes wherein the donor substituent serves as a nucleophile. The described annulation represents a convenient approach to bicyclo[3.2.1]octa-2,6-dienes with heteroarenes annulated to C(2)-C(3) bond. Its efficiency was demonstrated for a series of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, and indolyl substituted cyclopropanes. Additionally, in the case of 2-(5-methyl-2-furyl)cyclopropane-1,1-diester we observed the predominant formation of product of the [3+4] annulation or the tetracyclic 5,8-methanocyclopenta[a]azulene derivative, depending on the reaction conditions.
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GOST
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Ivanova O. et al. Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene // Advanced Synthesis and Catalysis. 2011. Vol. 353. No. 7. pp. 1125-1134.
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Ivanova O., Budynina E. M., Chagarovskiy A. O., Kaplun A. E., Trushkov I. V., Melnikov M. Y. Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene // Advanced Synthesis and Catalysis. 2011. Vol. 353. No. 7. pp. 1125-1134.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.201000783
UR - https://doi.org/10.1002/adsc.201000783
TI - Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene
T2 - Advanced Synthesis and Catalysis
AU - Ivanova, Olga
AU - Budynina, Ekaterina M
AU - Chagarovskiy, Alexey O
AU - Kaplun, Alexey E
AU - Trushkov, Igor V
AU - Melnikov, Mikhail Y.
PY - 2011
DA - 2011/05/03
PB - Wiley
SP - 1125-1134
IS - 7
VL - 353
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2011_Ivanova,
author = {Olga Ivanova and Ekaterina M Budynina and Alexey O Chagarovskiy and Alexey E Kaplun and Igor V Trushkov and Mikhail Y. Melnikov},
title = {Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene},
journal = {Advanced Synthesis and Catalysis},
year = {2011},
volume = {353},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/adsc.201000783},
number = {7},
pages = {1125--1134},
doi = {10.1002/adsc.201000783}
}
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MLA
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Ivanova, Olga, et al. “Lewis Acid-Catalyzed [3+4] Annulation of 2-(Heteroaryl)- cyclopropane-1,1-dicarboxylates with Cyclopentadiene.” Advanced Synthesis and Catalysis, vol. 353, no. 7, May. 2011, pp. 1125-1134. https://doi.org/10.1002/adsc.201000783.