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Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles

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Abstract

A convenient protocol for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines with various electron-withdrawing substituents at C-2 atom is described. This approach is based on the two-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines with α,β-unsaturated ketones, nitroalkenes and acrylonitrile. Depending on the selected substrates, the reaction was performed in TFE under reflux or under microwave irradiation. Only for the two examples, a transition metal catalyst was used.

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Acknowledgements

This work has been supported by the «RUDN University Program 5-100». The elemental analysis was performed using the equipment of the Center for Molecular Composition Studies at the INEOS RAS under support of the Ministry of Science and Higher Education of the Russian Federation.

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  1. Department of Organic Chemistry, Peoples’ Friendship, University of Russia (RUDN University), Miklukho-Maklaya st 6, Moscow, Russia, 117198

    Grigorii S. Astakhov, Rinat R. Shigaev, Tatiana N. Borisova, Anastasia A. Ershova, Alexander A. Titov, Alexey V. Varlamov, Leonid G. Voskressensky & Maria D. Matveeva

  2. Laboratory of Metal Hydrides (MHLab), A. N. Nesmeyanov Institute of Organoelement Compounds (INEOS), Russian Academy of Sciences, Vavilov St. 28, GSP-1, B-334, Moscow, Russia, 119991

    Grigorii S. Astakhov

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  1. Grigorii S. Astakhov
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Astakhov, G.S., Shigaev, R.R., Borisova, T.N. et al. Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles. Mol Divers 25, 2441–2446 (2021). https://doi.org/10.1007/s11030-020-10146-7

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