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Reactions of substituted 1,3- and 1,4-phenylenediamines with sodium azide and triethyl orthoformate in the presence of acetic acid led to the formation in high yields of the corresponding 1,12 -phenylenebis(1Htetrazoles). The presence of electron-acceptor groups in the molecules of the initial diamines reduces the yield of the target heterocycles. With 2-nitro-1,4-phenylenediamine the prevailing product was 2-nitro-4-(1H-tetrazol-1-yl)aniline. The obtained bistetrazoles in basic environment suffer an opening of one or both heterocycles forming cyanamides.

Reactions of phenylenediamines with sodium azide and triethyl orthoformate provides the title bis(tetrazoles), which suffer tetrazole opening under basic conditions.