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One-pot synthesis of novel fused pentacyclic chromenopyrimidobenzimidazolones and benzimidazolyl-chromenyl-substituted thiazolidinones

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Abstract The ultrasound promoted synthesis of a number of novel fused pentacyclic chromenopyrimido[1,2- α ]benzimidazolones by the one-pot reaction of 3-formylchromones with 2-aminobenzimidazole is described. Moreover, the isolated pentacyclic chromone… Click to show full abstract

Abstract The ultrasound promoted synthesis of a number of novel fused pentacyclic chromenopyrimido[1,2- α ]benzimidazolones by the one-pot reaction of 3-formylchromones with 2-aminobenzimidazole is described. Moreover, the isolated pentacyclic chromone derivatives upon microwave irradiation with 2-mercaptocarboxylic acids afforded benzimidazolyl-chromenylthiazolidinones incorporating three pharmacophoric heterocycles; the same thiazolidinones were also formed through a multicomponent reaction under microwave irradiation involving 3-formylchromones, aminobenzimidazole and 2-mercaptocarboxylic acids. The structural elucidation of the products was accomplished by 1D and 2D NMR experiments and for thiazolidinones was also confirmed by X-ray crystallographic analysis. Full assignment of all 1 H and 13 C NMR chemical shifts has been unambiguously achieved. The proposed reaction mechanism is also discussed.

Keywords: fused pentacyclic; novel fused; synthesis; one pot

Journal Title: Tetrahedron
Year Published: 2017

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