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

✍ Scribed by Naomi Hunter; Keith Vaughan

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 431 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430330

✦ Synopsis

Abstract

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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.