Organic Letters

, volume 22 , issue 12 , pages 4726-4731

A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes

Nikita E Golantsov ¹

Alexandra S Golubenkova ¹

Alexey A. Festa ¹

Alexey V. Varlamov ¹

Leonid G. Voskressensky ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Organic Chemistry Department, Science Faculty, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russia |

Publication type: Journal Article

Publication date: 2020-06-02

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.0c01530

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PubMed ID: 32484359

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to an effective formation of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/transannular nucleophilic addition/oxidative ring opening reactions. The direct one-pot transformation of 2-imidazolines to pyrroles has been also realized.

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GOST |

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GOST Copy

Golantsov N. E. et al. A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes // Organic Letters. 2020. Vol. 22. No. 12. pp. 4726-4731.

GOST all authors (up to 50) Copy

Golantsov N. E., Golubenkova A. S., Festa A. A., Varlamov A. V., Voskressensky L. G. A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes // Organic Letters. 2020. Vol. 22. No. 12. pp. 4726-4731.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.0c01530

UR - https://doi.org/10.1021/acs.orglett.0c01530

TI - A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes

T2 - Organic Letters

AU - Golantsov, Nikita E

AU - Golubenkova, Alexandra S

AU - Festa, Alexey A.

AU - Varlamov, Alexey V.

AU - Voskressensky, Leonid G.

PY - 2020

DA - 2020/06/02

PB - American Chemical Society (ACS)

SP - 4726-4731

IS - 12

VL - 22

PMID - 32484359

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2020_Golantsov,

author = {Nikita E Golantsov and Alexandra S Golubenkova and Alexey A. Festa and Alexey V. Varlamov and Leonid G. Voskressensky},

title = {A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes},

journal = {Organic Letters},

year = {2020},

volume = {22},

publisher = {American Chemical Society (ACS)},

month = {jun},

url = {https://doi.org/10.1021/acs.orglett.0c01530},

number = {12},

pages = {4726--4731},

doi = {10.1021/acs.orglett.0c01530}

}

MLA

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MLA Copy

Golantsov, Nikita E., et al. “A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes.” Organic Letters, vol. 22, no. 12, Jun. 2020, pp. 4726-4731. https://doi.org/10.1021/acs.orglett.0c01530.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)