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A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines. / Mishina, Maria S.; Ivanov, Alexander Yu; Lobanov, Pavel S.; Dar'In, Dmitrii V.

In: Synthesis, Vol. 48, No. 17, ss-2016-z0140-op, 01.09.2016, p. 2851-2862.

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

Harvard

Mishina, MS, Ivanov, AY, Lobanov, PS & Dar'In, DV 2016, 'A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines', Synthesis, vol. 48, no. 17, ss-2016-z0140-op, pp. 2851-2862. https://doi.org/10.1055/s-0035-1561645, https://doi.org/10.1055/s-0035-1561645

APA

Mishina, M. S., Ivanov, A. Y., Lobanov, P. S., & Dar'In, D. V. (2016). A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines. Synthesis, 48(17), 2851-2862. [ss-2016-z0140-op]. https://doi.org/10.1055/s-0035-1561645, https://doi.org/10.1055/s-0035-1561645

Vancouver

Mishina MS, Ivanov AY, Lobanov PS, Dar'In DV. A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines. Synthesis. 2016 Sep 1;48(17):2851-2862. ss-2016-z0140-op. https://doi.org/10.1055/s-0035-1561645, https://doi.org/10.1055/s-0035-1561645

Author

Mishina, Maria S. ; Ivanov, Alexander Yu ; Lobanov, Pavel S. ; Dar'In, Dmitrii V. / A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines. In: Synthesis. 2016 ; Vol. 48, No. 17. pp. 2851-2862.

BibTeX

@article{7e6c9fbf28614c24841051c03812608f,
title = "A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines",
abstract = "An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and π-deficient 1,2-dihaloarenes is presented. The two-step methodology includes aromatic nucleophilic substitution of the activated halogen of dihaloarene with enediamine C-nucleophilic center followed by Cu-catalyzed intramolecular N-arylation. This approach allows access to a variety of 2-amino-6-nitroindoles and 6-aminopyrrolo[3,2-d]pyrimidines (including N-mono- and N,N-disubstituted) in moderate and good yields under mild conditions.",
keywords = "2-aminoindoles, copper catalyst, cyclization, geminal enediamines, N-arylation, pyrrolo[3,2- d ]pyrimidines",
author = "Mishina, {Maria S.} and Ivanov, {Alexander Yu} and Lobanov, {Pavel S.} and Dar'In, {Dmitrii V.}",
note = "Funding Information: We are grateful for the financial support from Saint Petersburg State University (Grant No. 12.38.195.2014). NMR and mass spectrometry studies were performed at Research Centre for Magnetic Resonance and Centre for Chemical Analysis and Materials Research of Saint Petersburg State University. Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart. New York. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",
year = "2016",
month = sep,
day = "1",
doi = "10.1055/s-0035-1561645",
language = "English",
volume = "48",
pages = "2851--2862",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "17",

}

RIS

TY - JOUR

T1 - A New Synthesis of 2-Aminoindoles and 6-Aminopyrrolo[3,2- d ]pyrimidines from π-Deficient 1,2-Dihaloarenes and Geminal Enediamines

AU - Mishina, Maria S.

AU - Ivanov, Alexander Yu

AU - Lobanov, Pavel S.

AU - Dar'In, Dmitrii V.

N1 - Funding Information: We are grateful for the financial support from Saint Petersburg State University (Grant No. 12.38.195.2014). NMR and mass spectrometry studies were performed at Research Centre for Magnetic Resonance and Centre for Chemical Analysis and Materials Research of Saint Petersburg State University. Publisher Copyright: © Georg Thieme Verlag Stuttgart. New York. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/9/1

Y1 - 2016/9/1

N2 - An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and π-deficient 1,2-dihaloarenes is presented. The two-step methodology includes aromatic nucleophilic substitution of the activated halogen of dihaloarene with enediamine C-nucleophilic center followed by Cu-catalyzed intramolecular N-arylation. This approach allows access to a variety of 2-amino-6-nitroindoles and 6-aminopyrrolo[3,2-d]pyrimidines (including N-mono- and N,N-disubstituted) in moderate and good yields under mild conditions.

AB - An efficient approach for the synthesis of fused 2-aminopyrroles via geminal enediamines and π-deficient 1,2-dihaloarenes is presented. The two-step methodology includes aromatic nucleophilic substitution of the activated halogen of dihaloarene with enediamine C-nucleophilic center followed by Cu-catalyzed intramolecular N-arylation. This approach allows access to a variety of 2-amino-6-nitroindoles and 6-aminopyrrolo[3,2-d]pyrimidines (including N-mono- and N,N-disubstituted) in moderate and good yields under mild conditions.

KW - 2-aminoindoles

KW - copper catalyst

KW - cyclization

KW - geminal enediamines

KW - N-arylation

KW - pyrrolo[3,2- d ]pyrimidines

UR - http://www.scopus.com/inward/record.url?scp=84969988810&partnerID=8YFLogxK

U2 - 10.1055/s-0035-1561645

DO - 10.1055/s-0035-1561645

M3 - Article

VL - 48

SP - 2851

EP - 2862

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 17

M1 - ss-2016-z0140-op

ER -

ID: 7631056