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Synthesis of new isatin derivatives for possible CNS activity


Master's Thesis from the year 2013 in the subject Medicine - Pharmacology, grade: 10, , course: M-Pharmacy, language: English, abstract: Isatin (1H-indole-2,3-dione) (I) was first discovered by Erdmann and Laurent in 1841, independently as a product from oxidation of indigo by nitric and chromic acids. It is a unique molecule possessing both amide and keto carbonyl groups. Apart from this, it has an active hydrogen atom attached to nitrogen (or oxygen) and an aromatic ring which was substituted at 5- and 7-positions. It exists in a tautomeric form (II) and these functional characteristics play an important role in governing the various reactions of the molecule. The C-3 carbonyl group of isatin is strongly electrophilic. As a result, isatins are readily involved in condensation and addition reactions with carbanion type nucleophiles into 3-substituted oxindoles. In general, there are three possibilities during condensation reactions. [...]