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An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles. / Agafonova, Anastasiya V.; Funt, Liya D.; Novikov, Mikhail S.; Khlebnikov, Alexander F.

In: Organic and Biomolecular Chemistry, Vol. 19, No. 9, 07.03.2021, p. 1976-1984.

Research output: Contribution to journal › Article › peer-review

Harvard

Agafonova, AV, Funt, LD, Novikov, MS & Khlebnikov, AF 2021, 'An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles', Organic and Biomolecular Chemistry, vol. 19, no. 9, pp. 1976-1984. https://doi.org/10.1039/d1ob00053e

APA

Agafonova, A. V., Funt, L. D., Novikov, M. S., & Khlebnikov, A. F. (2021). An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles. Organic and Biomolecular Chemistry, 19(9), 1976-1984. https://doi.org/10.1039/d1ob00053e

Vancouver

Agafonova AV, Funt LD, Novikov MS, Khlebnikov AF. An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles. Organic and Biomolecular Chemistry. 2021 Mar 7;19(9):1976-1984. https://doi.org/10.1039/d1ob00053e

Author

Agafonova, Anastasiya V. ; Funt, Liya D. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. / An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles. In: Organic and Biomolecular Chemistry. 2021 ; Vol. 19, No. 9. pp. 1976-1984.

BibTeX

@article{c4dab3419a0c4a7494b719c52a655e7b,
title = "An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles",
abstract = "A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(ii) catalysis. Alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylate formation are presented.",
author = "Agafonova, {Anastasiya V.} and Funt, {Liya D.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.}",
note = "Funding Information: We gratefully acknowledge the financial support from the Russian Science Foundation (Grant no. 19-13-00039). This research used resources of the Magnetic Resonance Research Centre, Chemical Analysis, Materials Research Centre, Centre for X-ray Diffraction Studies, and the Computer Centre of the Science Park of Saint Petersburg State University. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",
year = "2021",
month = mar,
day = "7",
doi = "10.1039/d1ob00053e",
language = "English",
volume = "19",
pages = "1976--1984",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "9",

}

RIS

TY - JOUR

T1 - An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles

AU - Agafonova, Anastasiya V.

AU - Funt, Liya D.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

N1 - Funding Information: We gratefully acknowledge the financial support from the Russian Science Foundation (Grant no. 19-13-00039). This research used resources of the Magnetic Resonance Research Centre, Chemical Analysis, Materials Research Centre, Centre for X-ray Diffraction Studies, and the Computer Centre of the Science Park of Saint Petersburg State University. Publisher Copyright: © The Royal Society of Chemistry 2021. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/3/7

Y1 - 2021/3/7

N2 - A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(ii) catalysis. Alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylate formation are presented.

AB - A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(ii) catalysis. Alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylate formation are presented.

UR - http://www.scopus.com/inward/record.url?scp=85102372844&partnerID=8YFLogxK

U2 - 10.1039/d1ob00053e

DO - 10.1039/d1ob00053e

M3 - Article

AN - SCOPUS:85102372844

VL - 19

SP - 1976

EP - 1984

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -

ID: 75289470