Abstract
In order to prepare novel polycyclic derivatives of bicyclo[3.2.1]octadiene systems fused with a thiophene ring, photochemical cyclization and aldol condensation reactions were carried out. The starting substrates were easily obtained by a Vilsmeier–Haack reaction of bicyclo[3.2.1]octadiene thiophene derivatives with dimethylformamide. From the obtained carbaldehydes, novel methyl, methoxy, and cyano-substituted styryl thienobenzobicyclo[3.2.1]octadiene derivatives were synthesized through Wittig reactions and subjected to photochemical cyclization, in terms of obtaining the new annulated structures. As part of this study, the aldol reaction of the starting 2-substituted carbaldehyde with acetone was also performed, which produced the thieno-fused benzobicyclo[3.2.1]octadiene compound with an extended conjugation.
Highlights
The bicyclo[3.2.1]octane skeleton has become the subject of intensive research in recent years [1-3]
In order to prepare novel polycyclic derivatives of bicyclo[3.2.1]octadiene systems fused with a thiophene ring, photochemical cyclization and aldol condensation reactions were carried out
The starting substrates were obtained by a Vilsmeier–Haack reaction of bicyclo[3.2.1]octadiene thiophene derivatives with dimethylformamide
Summary
The bicyclo[3.2.1]octane skeleton has become the subject of intensive research in recent years [1-3]. Its presence in numerous biologically active natural compounds (Figure 1) [4-7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical methodology [8-21]. By using a simple photochemical procedure, it was possible to obtain a whole library of novel bicyclo[3.2.1]octadiene derivatives, available for further functionalization, which could enable the easier investigation of the relationship between structure and biological activity. During our previous investigation a series of Beilstein J.
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