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}

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M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russia, Fax: (+7)-495-939-1814 |

phone: (+7)-495-939-1316

M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russia, Fax: (+7)‐495‐939‐1814 |

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phone: (+7)‐495‐939‐1316

Publication type: Journal Article

Publication date: 2011-05-03

Wiley

Journal: Advanced Synthesis and Catalysis

Quartile SCImago

Quartile WOS

Impact factor: 5.4

ISSN: 16154150, 16154169

DOI: 10.1002/adsc.201000783

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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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European Journal of Organic Chemistry	European Journal of Organic Chemistry, 4, 7.27% European Journal of Organic Chemistry 4 publications, 7.27%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 3, 5.45% Angewandte Chemie - International Edition 3 publications, 5.45%
Angewandte Chemie	Angewandte Chemie, 3, 5.45% Angewandte Chemie 3 publications, 5.45%
RSC Advances	RSC Advances, 2, 3.64% RSC Advances 2 publications, 3.64%
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Russian Chemical Reviews	Russian Chemical Reviews, 2, 3.64% Russian Chemical Reviews 2 publications, 3.64%
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Synlett	Synlett, 2, 3.64% Synlett 2 publications, 3.64%
Russian Chemical Bulletin	Russian Chemical Bulletin, 1, 1.82% Russian Chemical Bulletin 1 publication, 1.82%
ACS Catalysis	ACS Catalysis, 1, 1.82% ACS Catalysis 1 publication, 1.82%
Mendeleev Communications	Mendeleev Communications, 1, 1.82% Mendeleev Communications 1 publication, 1.82%
Tetrahedron	Tetrahedron, 1, 1.82% Tetrahedron 1 publication, 1.82%
Israel Journal of Chemistry	Israel Journal of Chemistry, 1, 1.82% Israel Journal of Chemistry 1 publication, 1.82%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.82% Advanced Synthesis and Catalysis 1 publication, 1.82%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 1.82% Asian Journal of Organic Chemistry 1 publication, 1.82%
Chemical Record	Chemical Record, 1, 1.82% Chemical Record 1 publication, 1.82%
ChemInform	ChemInform, 1, 1.82% ChemInform 1 publication, 1.82%
Chemical Reviews	Chemical Reviews, 1, 1.82% Chemical Reviews 1 publication, 1.82%
Organic Process Research and Development	Organic Process Research and Development, 1, 1.82% Organic Process Research and Development 1 publication, 1.82%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 1.82% Journal of the American Chemical Society 1 publication, 1.82%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 1, 1.82% Russian Journal of Organic Chemistry 1 publication, 1.82%
AIP Conference Proceedings	AIP Conference Proceedings, 1, 1.82% AIP Conference Proceedings 1 publication, 1.82%
	1 2 3 4 5 6 7

Citations by publishers

	5 10 15 20 25
Wiley	Wiley, 22, 40% Wiley 22 publications, 40%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 11, 20% Royal Society of Chemistry (RSC) 11 publications, 20%
American Chemical Society (ACS)	American Chemical Society (ACS), 11, 20% American Chemical Society (ACS) 11 publications, 20%
Elsevier	Elsevier, 4, 7.27% Elsevier 4 publications, 7.27%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 2, 3.64% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 2 publications, 3.64%
Thieme	Thieme, 2, 3.64% Thieme 2 publications, 3.64%
Springer Nature	Springer Nature, 1, 1.82% Springer Nature 1 publication, 1.82%
Pleiades Publishing	Pleiades Publishing, 1, 1.82% Pleiades Publishing 1 publication, 1.82%
American Institute of Physics (AIP)	American Institute of Physics (AIP), 1, 1.82% American Institute of Physics (AIP) 1 publication, 1.82%
	5 10 15 20 25

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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.

GOST all authors (up to 50) Copy

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.

RIS |

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 00:00:00

PB - Wiley

SP - 1125-1134

IS - 7

VL - 353

SN - 1615-4150

SN - 1615-4169

ER -

BibTex |

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BibTex Copy

@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}

}

MLA

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MLA Copy

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.

Found error?

Publisher

Wiley

Journal

Advanced Synthesis and Catalysis

Quartile SCImago

Quartile WOS

Impact factor

5.4

ISSN

16154150 (Print)
16154169 (Electronic)