Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

Qian Wang; Angelina Osipyan; Markella Konstantinidou; Roberto Butera; Kumchok C. Mgimpatsang; Svitlana V. Shishkina; Alexander Dömling

doi:10.1021/acs.joc.9b01258

Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

Qian Wang, Angelina Osipyan, Markella Konstantinidou, Roberto Butera, Kumchok C. Mgimpatsang, Svitlana V. Shishkina, Alexander Dömling^*

^*Corresponding author for this work

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

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Abstract

Here we describe a facile, tandem synthetic route for indolo[3,2-c]quinolinones, a class of natural alkaloid analogues of high biological significance. A Ugi four-component reaction with indole-2-carboxylic acid and an aniline followed by a Pd-catalyzed cyclization yields tetracyclic indoloquinolines in good to moderate yields. Commercially available building blocks yield highly diverse analogues in just two simple steps.

Original language	English
Pages (from-to)	12148-12156
Number of pages	9
Journal	The Journal of Organic Chemistry
Volume	84
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.9b01258
Publication status	Published - 20-Sept-2019

Keywords

article
catalysis
2 indolecarboxylic acid
alkaloid
aniline
MULTICOMPONENT REACTIONS
INHIBITORS
DESIGN

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10.1021/acs.joc.9b01258Licence: CC BY-NC-ND

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16 Citations
1 Erratum

Correction to Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles
Wang, Q., Osipyan, A., Konstantinidou, M., Butera, R., Mgimpatsang, K. C., Shishkina, S. V. & Dömling, A., 19-Jun-2020, In: The Journal of Organic Chemistry. 85, 12, p. 8295 1 p., 8295.
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CCDC 1912181: Experimental Crystal Structure Determination
Wang, Q. (Contributor), Osipyan, A. (Contributor), Konstantinidou, M. (Contributor), Butera, R. (Contributor), Mgimpatsang, K. C. (Contributor), Shishkina, S. V. (Contributor) & Dömling, A. (Contributor), University of Groningen, 25-Apr-2019
DOI: 10.5517/ccdc.csd.cc225s8b
Dataset
CCDC 1912182: Experimental Crystal Structure Determination
Wang, Q. (Contributor), Osipyan, A. (Contributor), Konstantinidou, M. (Contributor), Butera, R. (Contributor), Mgimpatsang, K. C. (Contributor), Shishkina, S. V. (Contributor) & Dömling, A. (Contributor), University of Groningen, 25-Apr-2019
DOI: 10.5517/ccdc.csd.cc225s9c
Dataset

Cite this

@article{562aa1224bb94043a503b968384c7574,

title = "Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles",

abstract = "Here we describe a facile, tandem synthetic route for indolo[3,2-c]quinolinones, a class of natural alkaloid analogues of high biological significance. A Ugi four-component reaction with indole-2-carboxylic acid and an aniline followed by a Pd-catalyzed cyclization yields tetracyclic indoloquinolines in good to moderate yields. Commercially available building blocks yield highly diverse analogues in just two simple steps.",

keywords = "article, catalysis, 2 indolecarboxylic acid, alkaloid, aniline, MULTICOMPONENT REACTIONS, INHIBITORS, DESIGN",

author = "Qian Wang and Angelina Osipyan and Markella Konstantinidou and Roberto Butera and Mgimpatsang, {Kumchok C.} and Shishkina, {Svitlana V.} and Alexander D{\"o}mling",

year = "2019",

month = sep,

day = "20",

doi = "10.1021/acs.joc.9b01258",

language = "English",

volume = "84",

pages = "12148--12156",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

AU - Wang, Qian

AU - Osipyan, Angelina

AU - Konstantinidou, Markella

AU - Butera, Roberto

AU - Mgimpatsang, Kumchok C.

AU - Shishkina, Svitlana V.

AU - Dömling, Alexander

PY - 2019/9/20

Y1 - 2019/9/20

N2 - Here we describe a facile, tandem synthetic route for indolo[3,2-c]quinolinones, a class of natural alkaloid analogues of high biological significance. A Ugi four-component reaction with indole-2-carboxylic acid and an aniline followed by a Pd-catalyzed cyclization yields tetracyclic indoloquinolines in good to moderate yields. Commercially available building blocks yield highly diverse analogues in just two simple steps.

AB - Here we describe a facile, tandem synthetic route for indolo[3,2-c]quinolinones, a class of natural alkaloid analogues of high biological significance. A Ugi four-component reaction with indole-2-carboxylic acid and an aniline followed by a Pd-catalyzed cyclization yields tetracyclic indoloquinolines in good to moderate yields. Commercially available building blocks yield highly diverse analogues in just two simple steps.

KW - article

KW - catalysis

KW - 2 indolecarboxylic acid

KW - alkaloid

KW - aniline

KW - MULTICOMPONENT REACTIONS

KW - INHIBITORS

KW - DESIGN

U2 - 10.1021/acs.joc.9b01258

DO - 10.1021/acs.joc.9b01258

M3 - Article

SN - 0022-3263

VL - 84

SP - 12148

EP - 12156

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 18

ER -

Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

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Datasets

CCDC 1912181: Experimental Crystal Structure Determination

CCDC 1912182: Experimental Crystal Structure Determination

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