Extended Multicomponent Reactions with Indole Aldehydes: Access
to Unprecedented Polyheterocyclic Scaffolds, Ligands of the
Aryl Hydrocarbon Receptor

J 2021

Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor

GHASHGHAEI, O., M. PEDROLA, F. SEGHETTI, V.V. MARTIN, R. ZAVARCE et. al.

Základní údaje

Originální název

Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor

Autoři

GHASHGHAEI, O., M. PEDROLA, F. SEGHETTI, V.V. MARTIN, R. ZAVARCE, Michal BABIAK (703 Slovensko, domácí), Jiří NOVÁČEK (203 Česká republika, garant, domácí), F. HARTUNG, K.M. ROLFES, T. HAARMANN-STEMMANN a R. LAVILLA

Vydání

Angewandte Chemie International Edition, WEINHEIM (GERMANY), Verlag Chemie, 2021, 1433-7851

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 16.823

Kód RIV

RIV/00216224:14740/21:00121237

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/anie.202011253

UT WoS

000592223900001

Klíčová slova anglicky

domino reactions; multicomponent reactions; nitrogen heterocycles; receptors; synthetic methods

Štítky

CF CRYO, rivok

Změněno: 27. 10. 2024 14:12, Ing. Martina Blahová

Anotace

V originále

The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke-Blackburn-Bienayme reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet-Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.

Návaznosti

90127, velká výzkumná infrastruktura

Název: CIISB II

Citovat

GHASHGHAEI, O., M. PEDROLA, F. SEGHETTI, V.V. MARTIN, R. ZAVARCE, Michal BABIAK, Jiří NOVÁČEK, F. HARTUNG, K.M. ROLFES, T. HAARMANN-STEMMANN a R. LAVILLA. Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor. Angewandte Chemie International Edition. WEINHEIM (GERMANY): Verlag Chemie, 2021, roč. 60, č. 5, s. 2603-2608. ISSN 1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.202011253.

@article{1752576,
   author = {Ghashghaei, O. and Pedrola, M. and Seghetti, F. and Martin, V.V. and Zavarce, R. and Babiak, Michal and Nováček, Jiří and Hartung, F. and Rolfes, K.M. and HaarmannandStemmann, T. and Lavilla, R.},
   article_location = {WEINHEIM (GERMANY)},
   article_number = {5},
   doi = {http://dx.doi.org/10.1002/anie.202011253},
   keywords = {domino reactions; multicomponent reactions; nitrogen heterocycles; receptors; synthetic methods},
   language = {eng},
   issn = {1433-7851},
   journal = {Angewandte Chemie International Edition},
   title = {Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor},
   url = {https://onlinelibrary.wiley.com/doi/10.1002/anie.202011253},
   volume = {60},
   year = {2021}
}

TY  - JOUR
ID  - 1752576
AU  - Ghashghaei, O. - Pedrola, M. - Seghetti, F. - Martin, V.V. - Zavarce, R. - Babiak, Michal - Nováček, Jiří - Hartung, F. - Rolfes, K.M. - Haarmann-Stemmann, T. - Lavilla, R.
PY  - 2021
TI  - Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor
JF  - Angewandte Chemie International Edition
VL  - 60
IS  - 5
SP  - 2603-2608
EP  - 2603-2608
PB  - Verlag Chemie
SN  - 14337851
KW  - domino reactions
KW  - multicomponent reactions
KW  - nitrogen heterocycles
KW  - receptors
KW  - synthetic methods
UR  - https://onlinelibrary.wiley.com/doi/10.1002/anie.202011253
N2  - The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke-Blackburn-Bienayme reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet-Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.
ER  -

GHASHGHAEI, O., M. PEDROLA, F. SEGHETTI, V.V. MARTIN, R. ZAVARCE, Michal BABIAK, Jiří NOVÁČEK, F. HARTUNG, K.M. ROLFES, T. HAARMANN-STEMMANN a R. LAVILLA. Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor. \textit{Angewandte Chemie International Edition}. WEINHEIM (GERMANY): Verlag Chemie, 2021, roč.~60, č.~5, s.~2603-2608. ISSN~1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.202011253.

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