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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