Aqueous single step synthesis and structural characterization of allylated, propargylated, and benzylated 3-substituted 3-aminooxindoles

ABSTRACT

Efficient zinc-mediated allylation, propargylation, and benzylation of isatin-derived imines were undertaken for the synthesis of 3-substituted 3-aminooxindoles with ≈80% yield. Such alternative approach has efficiently avoided the use of catalysts, severe reaction conditions, multistep procedures, and reaction additives. For exploring and materializing the synthetic utility, different allyl, propargyl, and benzyl bromides were used for generalizing the synthetic route. The structure of the synthesized compounds was established and confirmed by ¹H NMR, ¹³C NMR, FTIR, and mass spectroscopic techniques.

GRAPHICAL ABSTRACT

KEYWORDS:

• Allylation
• Barbier-type reaction
• benzylation
• propargylation
• 3-substituted 3-aminooxindoles

Acknowledgment

Authors are thankful to the Central University of Gujarat, Gandhinagar for infrastructural support and experimental facilities.