An Unusual Formation of 5-Phenyltetrazole in Reaction of Phenylacetylene with Dimethylammonium Azide
نویسندگان
چکیده
It is known that ammonium azides are both effective and convenient azidation agents, which are widely used in the syntheses of tetrazoles in media of aprotic dipolar solvents. However, until the present time, information about using these reagents for the synthesis of the 1,2,3-triazoles has been absent. In this case, alkali metal azides as well as trimethylsilyzide are the best known azidation agents. Here, we have considered the 1,3-dipolar cycloaddition reaction of dimethylammonium azide to phenylacetylene in DMF solution. We have applied the typical conditions for azidation reaction of acetylenes or nitriles in aprotic dipolar solvents: stirring at 120 °C for 10 hours with 1,2 molar excess amount of azidation agent. After mixing the reaction mass with cold water and double treating with ether, the aqueous layer was acidified by HCl to pH 3. The precipitate contained two compounds (TLC), which were separated by efficient crystallization from ethylacetate and ethanol and idenCROATICA CHEMICA ACTA CCACAA 72 (4) 953¿955 (1999)
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