| 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. |
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@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.
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