Triazines and related products. Part 18. Decomposition of 1,2,3-benzotriazines and related triazenes with sodium azide in acetic acid: a convenient route to azidoarenes

Abstract

1,2,3-Benzotriazin-4(3H)-one and its 3-aryl derivatives decompose in boiling acetic acid containing sodium azide or sodium iodide to afford 2-azido- and 2-iodo-benzamides, respectively, in high yields. Certain azidoarenes with nucleophilic ortho-substituents, formed from the decomposition of 1,2,3-benzotriazines and related aryltriazenes, cyclise with elimination of nitrogen under the reaction conditions. 1,2-Bis-o-nitrophenyltriazene in acetic acid containing sodium azide yields benzofurazan N-oxide and 2-nitroaniline.