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The reaction of bis([1,3,4]thiadiazolo)[1,3,5]triazinium bromides 3 with 1H[1,2,4]triazole 6, imidazole 7, 1-methylimidazole 8, and benzimidazole 9 in pyridine solution yielded product mixtures containing the highly substituted guanidines N-[[(1H-azolyl)[1,3,4]thiadiazol-3(2H)yl]methylene][1,3,4]thiadiazol-2-amines 10, 11, 12 as main products, and varying amounts 2[[1,3,4]thiadiazol-2-yl)imino][1,3,4]thiadiazol-3(2H-yl][1,3,4]thiadiazol-2(3H)-ones 13, 14, 15, and bis[2,3-dihydro[(5-methyl[1,3,4]thiadiazol-2-yl)imino][1,3,4]thiadiazol-3-yl]methanes 16, 17, 18 [bis(azolyl)alkanes, “aminals”], which were easily separated by column chromatography. The formation of the products appears to be the result of a novel SN(ANRORC) reaction cascade which competes with an azole catalyzed reaction. The latter causes partially ring destruction of 3.

Bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides 4.1 Syntheses of azole-substituted guanidines and bis(azolyl)alkanes