Domino Synthesis Of Novel Heterocyclic Compounds Based On 2-Hydroxychalcones

Bicyclo[3.3.1]nonane derivatives play a great role in host-guest chemistry, asymmetric catalysis and drug synthesis areas because of its V-shaped rigid structure. In this regard, the development of novel synthetic strategy for the clean and efficient approaches to bicyclic[3.3.1]nonanes is highly desirable. In this paper, our projects are focused on the highly efficient domino synthesis of bicyclic[3.3.1]nonanes based on 2-hydroxychalcones, and the details are as follows:In chapter one, the synthesis of 2,8-dioxabicyclo[3.3.1]nonanes, 2,8-oxazabicyclo[3.3.1]nonanes and other bicyclo[3.3.1]nonanes are summarized. Subsequently, our idea is given according to the above reviews.In chapter two, a simple and efficient method for the synthesis of functionalized di-aromatic ring-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives catalyzed by silver triflate from easily available 2-hydroxychalcones and naphthols/substituted phenols is described. Two six-membered cycles are formed in a one-pot operation. This reaction is probably achieved via a Michael addition/bicyclization domino process. Compounds are characterized by 1H NMR, 13 C NMR, IR, HRMS and X-ray single crystal diffraction.In chapter three, a simple and efficient method for one-pot synthesis of new functionalized 2,8-oxazabicyclo[3.3.1]nonanes from easily accessible 2-hydroxychalcones, 4-hydroxy coumarin/1,3-cyclohexandiones and aqueous ammonia under catalyst-free conditions is described. This reaction was probably achieved via an intermolecular Michael addition/amination/ intramolecular bicyclization domino process. Hydroxy-containing 5H-indeno-[1,2-b]pyridin-5-ones were obtained when five-membered 1,3-indandione was employed in this reaction. Compounds were characterized by 1H NMR, 13 C NMR, IR, HRMS and X-ray single crystal diffraction.In chapter four, a clean and efficient method for the domino synthesis of new functionalized benzofuro[2,3-c]pyridines from easily accessible 2-hydroxychalcones, α-bromo ketones and ammonium acetate is described. Furan and pyridine ring moieties are ingeniously formed in a one-pot operation in this tricyclic system. Compounds are characterized by 1H NMR, 13 C NMR, IR, HRMS and X-ray single crystal diffraction.In chapter five, a simple method for the synthesis of novel chromeneindanedione derivatives has been developed by the reaction of 2-hydroxychalcones with 1,3-indanedione in reflux toluene under catalyst-free conditions. This reaction probably undergoes a domino Michael addition/cyclization/oxidation process. All the compounds are characterized by 1H NMR、13C NMR、IR and HRMS. The UV-vis spectroscopy indicated that the maximum absorption wavelengths of the novel chromene-indanedione derivatives are at the range of 464~482 nm.