Reactions of substituted 2,3-dihydro-1H-indol-3-ones and pyrrolo[2,3-b]pyridin-3-ones with Wittig and Horner–Emmons reagents: synthesis of 7-azatryptamine

The reactivity of indolinone 1 towards Wittig and Horner–Emmons reactions was reported; the influence of the nature of substituent on the nitrogen atom was examined. 7-Azaindolinone 2 reacted with diethyl cyanomethanephosphonate for giving the corresponding (7-azaindol-3-yl)acetonitrile or more unexpectedly, a C-2 alkylated product; this behavior has been extended to another nucleophilic reagent. Finally the synthesis of 7-azatryptamine was reported.