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Cyclization of 5,6-Diarylpyrrolo[3,4-d]pyrimidine-2,4-diones into Pyrrolo[1,2-f]phenanthridine Derivatives: Intramolecular C–H Arylation under Ru/NHC Catalysis

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Abstract

The cyclization of 5,6-diarylpyrrolo[3,4-d]pyrimidine-2,4-diones containing a halogen atom in the ortho-position of one of the aryl rings, proceeding as intramolecular C–H arylation catalyzed by Ru(II) complexes, was studied. It was found that complexes Ru(NHC)(cymene)Cl2, where NHC = IPr [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], IMes [1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene], and their derivatives containing substituents at positions 4 and 5 of the imidazole ring, exhibit high catalytic activity. Based on the reaction studied, new representatives of pyrimido[5',4':3,4]pyrrolo[1,2-f]phenanthridine were obtained.

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ACKNOWLEDGMENTS

The authors express their gratitude to Academician of the Russian Academy of Sciences, prof. V.P. Ananikov for discussion of the results of the work and valuable comments. The authors also thank the Center for Collective Use “Nanotechnologies” of the Platov South-Russian State Polytechnic University and the Center for Collective Use of the N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences for performing analytical experiments.

Funding

The work was carried out with financial support from the Russian Science Foundation (project 22-23-00304).

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Authors and Affiliations

  1. Platov South-Russian State Polytechnic University (NPI), 346428, Novocherkassk, Russia

    Yu. N. Tkachenko, M. A. Shevchenko, I. V. Lavrentev, D. V. Pasyukov & V. M. Chernyshev

  2. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 119991, Moscow, Russia

    M. E. Minyaev

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  1. Yu. N. Tkachenko
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Correspondence to M. A. Shevchenko.

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Tkachenko, Y.N., Shevchenko, M.A., Lavrentev, I.V. et al. Cyclization of 5,6-Diarylpyrrolo[3,4-d]pyrimidine-2,4-diones into Pyrrolo[1,2-f]phenanthridine Derivatives: Intramolecular C–H Arylation under Ru/NHC Catalysis. Russ J Gen Chem 94, 327–336 (2024). https://doi.org/10.1134/S1070363224020087

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