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; Jiří NOVÁČEK; 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

https://doi.org/10.1002/anie.202011253

UT WoS

000592223900001

EID Scopus

2-s2.0-85096681228

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://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 = {https://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://doi.org/10.1002/anie.202011253.

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