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Solvent-free and transition metal catalyst-free synthesis of indolo[1,2-f]phenanthridine from 6-chlorophenanthridine

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Abstract

A new easily scalable synthesis of the important for materials chemistry indolo[1,2-f]phenanthridine from commercially available 6-chlorophenanthridine was developed. The suggested transition metal catalyst-free and solvent-free procedure is more ecologically friendly and cost efficient then the known methods. The yields of indolo[1,2-f]phenanthridine synthesized from 6-chlorophenanthridine in three steps were 20% and 26% if the cyclization was carried out solvent-free and in THF in the presence of lithium 2,2,6,6-tetramethylpiperidide, respectively.

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Authors and Affiliations

  1. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prosp., 119991, Moscow, Russian Federation

    G. K. Sterligov, A. N. Lysenko, E. A. Drokin, L. I. Minaeva, M. A. Topchiy, A. A. Ageshina, S. A. Rzhevskiy, M. S. Nechaev & A. F. Asachenko

  2. Department of Chemistry, Lomonosov Moscow State University, Build. 1, 3 Leninskie Gory, 119991, Moscow, Russian Federation

    M. S. Nechaev

Authors
  1. G. K. Sterligov
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  2. A. N. Lysenko
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  3. E. A. Drokin
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  4. L. I. Minaeva
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  5. M. A. Topchiy
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  6. A. A. Ageshina
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  7. S. A. Rzhevskiy
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  8. M. S. Nechaev
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  9. A. F. Asachenko
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Correspondence to A. F. Asachenko.

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Additional information

This work was financially supported by the Russian Science Foundation (Project No. 17-13-01076). The starting compounds were synthesized in the framework of the State task of A. V. Topchiev Institute of Petrochemical Synthesis of the Russian Academy of Sciences. The work was carried out using equipment of the Center for the Collective Use of the Scientific Equipment of the IPS RAS “Analytical Center for Problems of Deep Oil Refining and Petrochemistry”.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 479–483, March, 2022.

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Sterligov, G.K., Lysenko, A.N., Drokin, E.A. et al. Solvent-free and transition metal catalyst-free synthesis of indolo[1,2-f]phenanthridine from 6-chlorophenanthridine. Russ Chem Bull 71, 479–483 (2022). https://doi.org/10.1007/s11172-022-3436-z

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  • DOI: https://doi.org/10.1007/s11172-022-3436-z

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