Thiazolidinedione–Isatin Conjugates via an Uncatalyzed Diastereoselective Aldol Reaction on Water

An
uncatalyzed aldol reaction of N-substituted thiazolidinediones
with isatin derivatives has been developed “on water”
to afford a new class of pharmacologically important thiazolidinedione–isatin
conjugates in excellent yields and diastereoselectivities. The isatin–thiazolidine
conjugate undergoes a catalyst-free stereoselective transfer aldol
reaction on water. Single-crystal X-ray studies reveal that the aldol
products can self-assemble to form supramolecular DNA “zipper”
like structures through intermolecular hydrogen bonds and aromatic π–π
interactions.