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Heating 4-nitronaphthalic anhydride in an excess of 3(5)-methylpyrazole gives only 4-(3-methylpyrazolyl-1)naphthalic anhydride, which is converted by butylamine into the known N-butylimide of 4-(3-methylpyrazolyl-1)naphthalic acid.

A number of previously undescribed bis(1′,8′-naphthoylene-1,2-benzimidazoles) were obtained by reaction of bis(o-phenylenediamines) with various structures with naphthalic anhydride. Under the same conditions, the reaction of o-phenylenediamine with naphthalene-1,4,5,8-tetracarboxylic acid dianhydride leads to a mixture of cis and trans isomers of bisbenzimidazobenzophenanthrolinedione. The spectral and thermal characteristics of the synthesized compounds were studied.

4-(5-Methyl-2-oxoazolyl)naphthalic anhydride was synthesized by condensation of 4-chloroformylnaphthalic anhydride with aminoacetone and subsequent cyclization of the resulting amide. Luminescing methyl-substituted N-phenylnaphthalimide and 1,8-naphthoylene-1′,2′-benzimidazple were obtained by condensation of this product with aniline and o-phenylenediamine, respectively. The relationship between the structures of the products and their electronic absorption and luminescence spectra was investigated.

The electronic nature of the substituent in naphthalic anhydride has a substantial effect on the isomeric composition of the naphthaloperinones formed in reactions with 1,8-naphthylenediamine. An electron-accepting substituent in the 4 position of naphthalic anhydride promotes predominant retention of the carbonyl group in the 1 position, while an electrondonating substituent promotes retention of the carbonyl group in the 8 position of the naphthalene ring. 10-Amino- and 11-amino-14H-benzo[4,5]isoquinolino[2,1-a]perimidin-14-ones were synthesized.