Redox Amination of Isatins

Abstract

This thesis details the development for the synthesis of oxindoles containing an N1-C3 bisindole linkage while simultaneously oxidizing an indoline to an indole. This bond is made via redox amination, meaning no external oxidants or reductants are needed. This method was found to be compatible with a wide range of isatins and was chosen as a strategy for synthesizing a library of oxindoles containing an N1-C3 linkage to either a pyrrole or an indole. Next is detailed attempts to extend the tert-amino effect to make pyrroles, along with unexpected results and preliminary findings. Finally, we report preliminary results on a Pd catalyzed decarboxylative amino allylation of isatins. In this methodology, an allyl amino ester is condensed with isatin. Upon treatment with Pd, decarboxylative allylation occurs to form a 3, 3 disubstituted oxindole containing an allyl group and a free amine. teh only Stoiciometric by-products from this reaction are CO2 and acetone.