The synthesis of four isomeric nitro deJqvatives of methyldiazaphenanthrenes (DAP) has been desoqbed. The UV spectra of these compounds have been recorded and compared with those of parent diazaphenanthrenes. The biological data of methylnitrodiazaphenanthrenes and of other derivatives of diazaphenanthrenes are presented. Azaaromatics are of interest as drugs [1-3], agrochemicals [4,5], dyes [6], catalysts [7,8], etc.; they are promising in the construction of electronic devices [9] and in the investigation ofbiomimetic processes [10]. The present paper is a continuation of our study of !,5-, 1,6-, and 4,6-diazaphenanthrenes (DAPs) 1-3 and their derivatives displaying biological activity [11-13]; due to the presence of two nitrogen atoms in the molecule, DAPs form complexes with transition metal ions [ 14] as well as quaternary salts [ 12,15] and N-oxides [ 13]. 2 8~N5 I 2 3Some quaternary salts of DAPs are precursors of ylides, useful in 1,3-dipolar cycloaddition reactions [16,17]. DAP N-oxides are of interest because of their reactivity [18,19]; methyiDAPs may be oxidized to corresponding aldehydes [ 11 ].NitroDAPs 4-6 [20] serve as starting materials for the synthesis of amino derivatives, undergoing a series of reactions [l 1,21]; for example, they may be submitted to ring annelation by the Skraup procedure, leading to pyridoDAPs [22]. The diazotization of aminoDAPs followed by coupling reactions affords azo dyes [23].
NO2 NO2
5 6The UV spectroscopy results have been reported for formyl [24], methyl [25, 26], bromo [27], and amino [28] derivatives of DAPs, as well as for their quaternary salts [29].