Heterocyclic analogs of pleiadiene |
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Authors: | A. I. Belyashova N. N. Zatsepina E. N. Malysheva A. F. Pozharskii L. P. Smirnova I. F. Tupitsyn |
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Affiliation: | (1) Rostov State University, 344006 Rostov-on-Don;(2) State Institute of Applied Chemistry, 197198 Leningrad |
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Abstract: | The behavior of N-methyl derivatives of perimidine (I), aceperimidine (VI), aceperimidylene (VII), naphth[2,3-d]imidazole (V), benzimidazole (II), and 1H- and 3H-naphth[1,2-d]imidazoles (III, IV) with respect to n-butyllithium was studied. Compounds I and V–VII add n-butyllithium to the C=N bond to give 2-n-butyl-2,3-dihydro derivatives, whereas II–IV are metallated to give 2-lithio derivatives. The different reactivities of I, V–VII, and II–IV are explained by the reduced aromatic character and high polarization of the C=N bond in I and V–VII. The investigated compounds are arranged in the following order with respect to the ease of undergoing basic deuterium exchange at the C-H bond V>II>III>IV>VII>I>VI. There is no correlation between the rate of deuterium exchange and the behavior of I–VII with respect to butyllithium.See [1] for communication XXX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1544–1548, November, 1977. |
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