Synthesis and characterization of a series of 1,x-bis-(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes

Reaction of isatoic anhydride with an alkanediamine in DMF solution under mild conditions affords excellent yields of the 1,x-bis-{(2-aminobenzoyl-)amino}alkanes (2a-k), which have been characterized by IR and NMR spectroscopy, high resolution mass spectrometry and elemental analysis. Diazotization of the bis-{(2-aminobenzoyl-)-amino}alkanes in aqueous solution gives high yields of the 1,x-bis-(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes (1a-k), whch have also been characterized by IR and NMR spectroscopy, high resolution mass spectrometry and elemental analysis. The alkanediamines employed are as follows: ethylene diamine, 1,3-propanediamine, 1,2-propanediamine, 2-methyl-1,2-propanediamine, 2,2-dimethyl-1,3-propanediamine, 2-hydroxy-1,3-propanediamine, 1,4-diaminobutane, 1,5-diaminopentane, 1,3-diaminopentane (DYTEK® EP diamine), 1,6-diaminohexane and 1,7-diaminoheptane. The alternative method of synthesis of the bis-(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes (1) via the diazonium salt from methyl anthranilate was explored.