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

Author： Borovlev I. V.   Demidov O. P.   Aksenov A. V.   Pozharskii A. F.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.40, Iss.6, 2004-06, pp. : 895-901

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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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