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6(7)-Acylperimidines nitration and methods of peri-annelation on this base

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Chemistry of Heterocyclic Compounds Aims and scope

A method has been developed for the nitration of 6(7)-acylperimidines using sodium nitrite in formic acid. The reaction gives a mixture of 4(9)-, 9(4)-, and 7(6)-nitro-6(7)-acylperimidines from which the latter can be separated by extraction with chloroform. Reduction of the 6(7)-acyl-7(6)-nitro- perimidines yields 1H-1,5,7-triazacyclopenta[cd]phenalenes. Subsequent Schmidt reaction and reduction give 1,3,6,8-tetraazapyrenes.

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This work was carried out with the financial support of the Russian Foundation for Basic Research (grant 12-03-31646mol_a)

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Authors and Affiliations

  1. North Caucasus Federal University, 1 Pushkin St., Stavropol, 355009, Russia

    A. V. Aksenov, N. A. Aksenov, A. S. Lyakhovnenko, A. N. Smirnov & I. V. Aksenova

  2. N. M. Emanuel Institute of Biochemical Physics, 4 Kosygin St., Moscow, 119991, Russia

    I. I. Levina

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  1. A. V. Aksenov
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  3. A. S. Lyakhovnenko
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Correspondence to A. V. Aksenov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1052-1059, July, 2013.

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Aksenov, A.V., Aksenov, N.A., Lyakhovnenko, A.S. et al. 6(7)-Acylperimidines nitration and methods of peri-annelation on this base. Chem Heterocycl Comp 49, 980–987 (2013). https://doi.org/10.1007/s10593-013-1335-9

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  • DOI: https://doi.org/10.1007/s10593-013-1335-9

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