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A Tandem Aldol-Diels-Alder Reaction Accelerated in Water: An Approach to the Catalyst-Free One-Pot Synthesis of Spiro Thio-Oxindoles

F. Matloubi Moghaddam*, L. Hojabri, S. Taheri and P. Pirani

Laboratory of Organic Synthesis & Natural Products, Department of Chemistry, Sharif University of Technology, P. O. Box 11155-9516, Tehran, Iran

Spiro thio-oxindoles are prepared in situ by the reaction of the corresponding aldehydes and thio-oxindoles in a straightforward, environmentally friendly, highly efficient and simple procedure. The reaction took place in water with no catalyst added. This one-pot reaction afforded regio- and diastereoselective products in high yields (61-93%).

Keywords: Spiro thio-oxindoles, Aldol-Diels-Alder reaction, Dimerization, α,β-Unsaturated thio-oxindole