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Amination of chloro-substituted heteroarenes with adamantane-containing amines

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Abstract

Amination of 3,6-dichloropyridazine, chloropyrazine, 2,3and 2,6-dichloropyrazines, 2-chloroquinoxaline, 1-chloroand 1,3-dichloroisoquinolines with various adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline, the chlorine atom at position 1 was selectively substituted in up to 90% yield.

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Authors and Affiliations

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

    A. S. Abel, O. K. Grigorova, A. D. Averin, O. A. Maloshitskaya & I. P. Beletskaya

  2. Volzhsky Polytechnical Institute (branch) of the Volgograd State Technical University, 42a ul. Engel’sa, 404121, Volzhsky, Volgograd Region, Russian Federation

    G. M. Butov

  3. Volgograd State Technical University, 28 prosp. Lenina, 400131, Volgograd, Russian Federation

    E. N. Savelyev, B. S. Orlinson & I. A. Novakov

Authors
  1. A. S. Abel
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  2. O. K. Grigorova
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  3. A. D. Averin
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  4. O. A. Maloshitskaya
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  5. G. M. Butov
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  6. E. N. Savelyev
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  7. B. S. Orlinson
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  8. I. A. Novakov
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  9. I. P. Beletskaya
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Corresponding author

Correspondence to A. D. Averin.

Additional information

Based on the materials of the International Congress on the Heterocyclic Chemistry “KOST-2015” (October 18–23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1820–1828, July, 2016.

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Abel, A.S., Grigorova, O.K., Averin, A.D. et al. Amination of chloro-substituted heteroarenes with adamantane-containing amines. Russ Chem Bull 65, 1820–1828 (2016). https://doi.org/10.1007/s11172-016-1516-7

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  • DOI: https://doi.org/10.1007/s11172-016-1516-7

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