Benzo perimidin-7-ones

Copper-catalyzed reaction of guanidine with l,4-dichloro-9,10-anthracenedione 928 in DMF not only resulted in formation of the targeted 777-benzo[i ]perimidin-7-one ring system, but also resulted in substitution of the second chlorine atom by a dimethylamino group from the DMF solvent to give 929 <2002BMC1025>. 

Monocyclic azines are very weak rr-donors and behave mostly as n-donors on interaction with electrophiles. However, ir-donor character is significantly increased in their benzo-derivatives. For instance, acridine forms with chloranil a highly colored 1 1 molecular complex. Perimidine is one of the strongest heterocyclic ir-donors which gives deeply colored molecular complexes with a variety of organic electron acceptors. On the other hand, the rr-acceptor ability of perimidine is moderate. 

Stefanska, B., Dzieduszycka, M., Martelli, S., Tarasiuk, J., Bontemps-Gracz, M. and Borowski, E. (1993) 6-[(Aminoalkyl)amino]-substituted 7H-benzo[e ]perimidin-7-ones as novel antineoplastic agents. Synthesis and biological evaluation. J. Med. Chem. 36 38-41. 

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