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Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives

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Abstract

Reactions of perimidines and perimidin-2-ones with α,β-unsaturated carbonyl compounds gave various 1,3-diazapyrene derivatives. Acylation of 1-methylperimidine, perimidin-2-one, and 1-methylperi-midin-2-one with cinnamoyl chloride in the presence of AlBr3 is accompanied by peri-fusion at the 6,7-position and dearylation of the intermediate product. Under analogous conditions, 1,3-dimethyl-2,3-dihydroperimidine gave rise to 6-cinnamoyl-1,3-dimethyl-2,3-dihydroperimidine. Reactions of perimidin-2-ones with 1,3-di-phenyl-2-propenone in polyphosphoric acid resulted in peri-fusion at the 6,7-position, and with acetylacetone, at the 1,9-position.

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Authors and Affiliations

  1. Stavropol' State University, ul. Pushkina 1, Stavropol', 355009, Russia

    I. V. Borovlev, O. P. Demidov & A. V. Aksenov

  2. Rostov State University, Rostov-on-Don, Russia

    A. F. Pozharskii

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  1. I. V. Borovlev
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  2. O. P. Demidov
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  3. A. V. Aksenov
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  4. A. F. Pozharskii
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Borovlev, I.V., Demidov, O.P., Aksenov, A.V. et al. Heterocyclic Analogs of Pleiadiene: LXXIV. peri-Cyclizations in the Perimidine Series. Synthesis of 1,3-Diazapyrene Derivatives. Russian Journal of Organic Chemistry 40, 895–901 (2004). https://doi.org/10.1023/B:RUJO.0000044557.95160.e5

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  • DOI: https://doi.org/10.1023/B:RUJO.0000044557.95160.e5

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