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

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• 作者：Nicolaos M. Drosos^a ; Chrisoula Kakoulidou^a ; Marianna Raftopoulou^a ; Julia Stephanidou-Stephanatou^a ; ; Constantinos A. Tsoleridis^a ; ^{tsolerid@chem.auth.gr} ; Antonis G. Hatzidimitriou^b
• 关键词：2-aminobenzimidazole ; Chromones ; Multicomponent reactions ; 2-mercaptocarboxylic acids ; Microwave/ultrasound irradiation
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：5 January 2017
• 年：2017
• 卷：73
• 期：1
• 页码：1-7
• 全文大小：718 K
• 卷排序：73

文摘

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 1H and 13C NMR chemical shifts has been unambiguously achieved. The proposed reaction mechanism is also discussed.