Tetrahedron

, volume 68 , issue 2 , pages 619-627

Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles

Arkady S Pilipenko ¹

Vladimir V Melchin ¹

IGOR V. TRUSHKOV ²

Dmitry A. Cheshkov ³

Alexander V Butin ^{1, 4}

Hide authors affiliations Show authors affiliations: 4 affiliations

Research Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, Moskovskaya 2, Krasnodar 350072, Russian Federation |

M.V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1/3, Moscow 119991, Russian Federation |

State Scientific Research Institute of Chemistry and Technology of Organoelement Compounds, Entuziastov shosse 38, Moscow 111123, Russian Federation |

⁴

Perm State University, Bukireva 15, Perm 614990, Russian Federation |

Publication type: Journal Article

Publication date: 2012-01-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2011.10.114

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

The acid-catalyzed rearrangement of 5-alkyl-2-[2-(sulfonylamino)phenyl]furans into 2-(2-oxoalkyl)indoles is described. When the N-sulfonyl group in the starting compounds was displaced by an N-acyl group, the corresponding indoles were not formed under the same reaction conditions due to the in situ indole deacylation and decomposition. The presence of an alkyl group at the C5 position of the furan ring is also crucial for the efficiency of the process. The discussed rearrangement provides a simple and efficient approach to 2-(2-oxoalkyl)indoles.

Found

5 citations

Uchuskin Maxim

🥼 🤝

PhD in Chemistry

56 publications, 781 citations

h-index: 16

Perm State National Research University

Research interests

Heterocyclic compounds

Organic synthesis

Synthetic Organic Chemistry

1 citation

Beloglazkina Elena

DSc in Chemistry, professor

297 publications, 3 270 citations, 11 reviews

h-index: 29

Lomonosov Moscow State University

1 citation

Gorbunova Yuliya

DSc in Chemistry, professor, full member of the Russian Academy of Sciences

284 publications, 4 417 citations, 65 reviews

h-index: 34

Lomonosov Moscow State University

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Lanthanides

Supramolecular chemistry

Tetrapyrrolic compounds

1 citation

Volcho Konstantin

DSc in Chemistry, professor of the Russian Academy of Sciences

279 publications, 3 913 citations, 65 reviews

h-index: 32

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Danilkina Natalia

45 publications, 638 citations

h-index: 14

Saint Petersburg State University

Research interests

Bioorganic chemistry

Click chemistry

Heterocyclic compounds

Medicinal Chemistry

Organic Chemistry

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 751 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Zubkov Fedor

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DSc in Chemistry, professor

240 publications, 3 229 citations, 19 reviews

h-index: 31

Peoples' Friendship University of Russia

Research interests

Organic Chemistry

1 citation

Gazizov Almir

🥼

DSc in Chemistry

157 publications, 895 citations, 23 reviews

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Heterocyclic compounds

Organic Chemistry

Organophosphorus chemistry

1 citation

Karasik Andrey

DSc in Chemistry, professor, associate member of the Russian Academy of Sciences

224 publications, 2 607 citations

h-index: 26

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Luminescence

Phosphorus ligands

1 citation

Dotsenko Viktor

DSc in Chemistry, professor

246 publications, 2 762 citations, 2 reviews

h-index: 22

North Caucasus Federal University

Kuban State University

Research interests

Active methylene compounds

Biological activity

Heterocyclic compounds

Malononitrile

Selenoamides

Thioamides

1 citation

Zagidullin Almaz

🥼 🤝

PhD in Chemistry

81 publications, 892 citations

h-index: 17

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

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

1 citation

Aksenov Aleksandr

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DSc in Chemistry, professor

245 publications, 2 202 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 743 citations

h-index: 30

Ural Federal University

1 citation

Ilkin Vladimir

PhD in Chemistry

16 publications, 193 citations

h-index: 7

Ural Federal University

Research interests

Catalysis

Heterocyclic compounds

Organic Chemistry

Synthetic Organic Chemistry

1 citation

Krylov Igor

PhD in Chemistry

80 publications, 1 903 citations, 18 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Green chemistry

Organic Chemistry

Organic electrochemistry

Organic synthesis

Photochemistry

Plant protection

1 citation

Nikitina Evgeniya

PhD in Chemistry, associate professor

84 publications, 809 citations

h-index: 17

Peoples' Friendship University of Russia

1 citation

Tikhomirov Alexander

🥼 🤝

DSc in Chemistry, associate professor

60 publications, 931 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

1 citation

Ivanov Andrey

55 publications, 541 citations

h-index: 12

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Buev Evgeny

PhD in Chemistry

31 publications, 351 citations, 2 reviews

h-index: 9

Ural Federal University

Research interests

Chemistry of nitrogen-containing heterocycles

Organic Chemistry

Organic synthesis

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GOST Copy

Pilipenko A. S. et al. Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles // Tetrahedron. 2012. Vol. 68. No. 2. pp. 619-627.

GOST all authors (up to 50) Copy

Pilipenko A. S., Melchin V. V., TRUSHKOV I. V., Cheshkov D. A., Butin A. V. Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles // Tetrahedron. 2012. Vol. 68. No. 2. pp. 619-627.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2011.10.114

UR - https://doi.org/10.1016/j.tet.2011.10.114

TI - Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles

T2 - Tetrahedron

AU - Pilipenko, Arkady S

AU - Melchin, Vladimir V

AU - TRUSHKOV, IGOR V.

AU - Cheshkov, Dmitry A.

AU - Butin, Alexander V

PY - 2012

DA - 2012/01/01

PB - Elsevier

SP - 619-627

IS - 2

VL - 68

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2012_Pilipenko,

author = {Arkady S Pilipenko and Vladimir V Melchin and IGOR V. TRUSHKOV and Dmitry A. Cheshkov and Alexander V Butin},

title = {Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles},

journal = {Tetrahedron},

year = {2012},

volume = {68},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/j.tet.2011.10.114},

number = {2},

pages = {619--627},

doi = {10.1016/j.tet.2011.10.114}

}

MLA

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MLA Copy

Pilipenko, Arkady S., et al. “Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles.” Tetrahedron, vol. 68, no. 2, Jan. 2012, pp. 619-627. https://doi.org/10.1016/j.tet.2011.10.114.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)