title: Thiazolidinedione-isatin conjugates via an uncatalyzed diastereoselective aldol reaction on water.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700032, India.
authors.forename: Sushovan
authors.initials: S
authors.lastname: Paladhi
authors.forename: Meeta
authors.initials: M
authors.lastname: Bhati
authors.forename: Deepanjan
authors.initials: D
authors.lastname: Panda
authors.forename: Jyotirmayee
authors.initials: J
authors.lastname: Dash
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D045162:Thiazolidinediones / Q000737:chemistry*; D014867:Water
chemical_list: D045162:Thiazolidinediones; D014867:Water; D007510:Isatin; D004247:DNA