The Journal of Organic Chemistry

Amination of arenes with electron-deficient azodicarboxylates

H Mitchell, Y Leblanc

Index: Mitchell, Helen; Leblanc, Yves Journal of Organic Chemistry, 1994 , vol. 59, # 3 p. 682 - 687

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Citation Number: 86

Abstract

that the nitration of indoles unsubstituted at the 2-position is problematic. In some cases only polymeric compounds are produced. 1 A few reports exist on the reaction of diethyl azodicarboxylate and indole molecules. ll In these reports, refluxing conditions in toluene or dioxane were required for the reaction to take place. It was found that BTCEAD adds to indole (32) in ether at 8" C to provide the 3-hydrazidoindole (34)(Scheme 1) in 68% yield. ...