Abstract
Tetracyanoethylene adducts of cycloalkanones, 1-(2-oxocycloalkyl)ethane-1,1,2,2-tetracarbonitriles, reacted with aqueous ammonia at room temperature to give, depending on the cycloalkane ring size and reaction conditions, three types of nitrogen-containing heterocyclic compounds. The reaction of tetracyanoethylene-cyclohexanone adducts with 20–25% aqueous ammonia afforded 10,11-diazatricyclo[5.3.2.01,6]-dodec-8-ene derivatives, whereas their seven- and eight-membered analogs were converted to pyrrolo[3,4-c]-pyridines under similar conditions. Treatment of 1-(2-oxocyclooctyl)ethane-1,1,2,2-tetracarbonitrile with 10–15% aqueous ammonia led to the formation of 2,5-diamino-3-(2-oxocyclooctyl)-3H-pyrrole-3,4-dicarbonitrile as a mixture of two diastereoisomers.
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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 4, pp. 547–553.
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This study was performed under support by President’s scholarship for young scientists and post-graduate students (project no. SP-2501.2016.4).
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No conflict of interests is declared by the authors.
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Belikov, M.Y., Ershov, O.V. Different Directions of the Reaction of 1-(2-Oxocycloalkyl)-ethane-1,1,2,2-tetracarbonitriles with Aqueous Ammonia. Russ J Org Chem 55, 456–461 (2019). https://doi.org/10.1134/S1070428019040067
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DOI: https://doi.org/10.1134/S1070428019040067