D. A. Lobach

Synthesis of N-Phenyl-1,5,7-Triazacyclopenta[cd]- Phenalenes by the Reaction of 1H-Perimidine Carbonyl Derivatives with Nitrobenzene

A [cd]-annelated indole structural framework is often met in natural and synthetic compounds which show a variety of biological activity [1-3]. In addition, as low toxicity analogs of acenapthenes and benzopyrenes, such polyheterocyclic molecules may in the future replace these widely used photochemical probes [4] and this makes them more attractive for medical applications. Similar structures can be used in nanotechnology for modeling the reactivity of azafullerenes [5] and atom-modified nanotubes [6]. We have previously reported development of a method for the direct peri annelation of a pyrrole ring to 1H-perimidine derivatives containing a functional group at position 6(7). Either 1,3,5-triazines in polyphosphoric acid (PPA) [7] or a combination of 1,3,5-triazines with sodium azide in PPA [8] have been used as reagents. The unsubstituted 1H-1,5,7-triazacyclopenta[cd]phenalene and derivatives of this heterocyclic

peri Annelation of Perimidines in Reactions with 1,3-Dicarbonyl Compounds*

A new approach to 1,3-diazapyrenes via peri annelation of perimidines with 1,3-dicarbonyl compounds is developed. It is demonstrated that this method has a number of advantages compared to a previously reported procedure employing chalcones as electrophilic components. The new method can be used for efficient double peri annelation of biperimidines with 1,3-dicarbonyl compounds affording 2,2′-bi-1,3-diazapyrenes.

SYNTHESIS OF 1-THIA-5,7-DIAZACYCLOPENTA(cd)- PHENALENES FROM 6(7)-DERIVATIVES OF PERIMIDINE

Electrochemical oxidation of 6(7)-benzoylperimidines was shown to involve two stages of single electron transfer. Based on cyclic voltammetry and microelectrolysis data, a synthetic method was developed for the peri annelation of thiophene ring to benzoyl derivatives of perimidine. A new method was proposed for the preparation of 1-thia-5,7-diazacyclopenta[cd]phenalenes by fusing 6(7)-carbonyl derivatives of perimidine with elemental sulfur.