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.

Basic information

Original name

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

Authors

GHASHGHAEI, O., M. PEDROLA, F. SEGHETTI, V.V. MARTIN, R. ZAVARCE, Michal BABIAK (703 Slovakia, belonging to the institution), Jiří NOVÁČEK (203 Czech Republic, guarantor, belonging to the institution), F. HARTUNG, K.M. ROLFES, T. HAARMANN-STEMMANN and R. LAVILLA

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 16.823

RIV identification code

RIV/00216224:14740/21:00121237

Organization unit

Central European Institute of Technology

DOI

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

UT WoS

000592223900001

Keywords in English

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

Abstract

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.

Links

90127, large research infrastructures

Name: 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 and 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, vol. 60, No 5, p. 2603-2608. ISSN 1433-7851. Available from: 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 and 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, vol.~60, No~5, p.~2603-2608. ISSN~1433-7851. Available from: https://dx.doi.org/10.1002/anie.202011253.

Detailed Information on Publication Record