1- Substituted-perimidin-2-ones

Other azines. 1-Substituted perimidines 180 are hydroxylated (KOH, 180C) to form 1-substituted perimidin-2-ones 181 in excellent yields via oxidation of the presumed initial adduct. 

As described in CHEC-11(1996), pyrimidine has one axis of symmetry, about the 2,5-axis, and has three different pairs of bond lengths and four different bond angles <1996CHEC-11(6)93>. 8ymmetry is lost on unequal substitution at the 4-and/or 6-position, and accordingly quinazoline lacks the symmetry of pyrimidine. Perimidine is symmetrical about the 2-position because of proton isomerization (prototropy), but this symmetry is lost on substitution other than at the 2-position. 

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>. 

Potassium cyanate, carbonic and chlorocarbonic esters, phosgene, or urea are used as cyclizing agents in the synthesis of perimidine-2-one 430 (X = X = NR, Y = O) and its derivatives from 1,8-naphthylene-diamines. Naphtho[substituted amino group in position 2 (X = Y = NH or Y = NR) are obtained on interaction of 1,8-naphthylenediamines with bromocyanogen, cyanoamide, 5-methylisothiourea, arylisothiocyanates, or dimethyltri-chloromethylamine. 

The structural similarity to azoles and the resemblance of many physicochemical properties allow one to consider peri-codensed NH-heterocycIes of the perimidine type (236) as analogues of azolo heterocycles (85KGS867). Under the action of MSH, perimidine and its substituted derivatives give the quaternary salt 237 in good yield (80KGS93 83CPB1378). One of these salts was converted to l-methyl-3-amino-2,3-... 

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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