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An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.

1,3-Diethyl-6-oxindolylidenetetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-dione with 2-propyl substituent at the nitrogen atom of oxindole fragment (1d) was identified previously as a lead compound in an antiproliferative agent discovery effort based on oxindolylidene derivatives of...

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