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Rearrangements of heterocyclic compounds containing isothiuronium side chain

Authors: Hanusek Jiří | Váňa Jiří | Sedlák Miloš

Year: 2011

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Rearrangements of heterocyclic compounds containing isothiuronium side chain	Synthesis of heterocyclic compounds can be, in principle, performed by the two methodical approaches. First, classical approach, consists in construction of the heterocyclic skeleton either by intramolecular or cycloaddition reactions, whereas the second one involves transformation of already existing heterocycle to give another heterocycle. Recently, we have studied the structure and reactivity of substituted S-(1-phenylpyrrolidin-2-on-3-yl)-, S-(1-phenylpiperidin-2-on-3-yl)- and S-(1-phenylazetidin-2-on-3-yl)- isothiuronium salts which, in weakly basic medium, undergo an intramolecular rearrangement to give substituted 2-imino-5-[2-(phenylamino)-C1-3-alkyl]-1,3-thiazolidin-4-ones. More recently, we have extended the scope of this transformation: replacing the γ-lactam ring with a γ-lactone ring. Under acid or base conditions the rearrangement provided not only expected 1,3-thiazolidin-4-ones but also another heterocycles.	isothiuronium salts, rearrangements, mechanism