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Paper | Regular issue | Vol 71, No. 10, 2007, pp.2183-2201
Published online, 20th July, 2007
DOI: 10.3987/COM-07-11109
Novel 2H-1,2,3-Triazole Sodium Complex from N-[2-Amino-1,2-dicyanovinyl]alkanamides

Amal Al-Azmi,* Paulson George, and Osman M. E. El-Dusouqui

*Chemistry Department, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait

Abstract

Diazotization at 0 oC of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) 1 using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.