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.

中文翻译：

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一种简单且易于执行的合成路线，以官能化的噻吩双环[3.2.1]辛二烯。

为了制备与噻吩环稠合的双环[3.2.1]辛二烯系统的新型多环衍生物，进行了光化学环化和醛醇缩合反应。通过双环[3.2.1]辛二烯噻吩衍生物与二甲基甲酰胺的Vilsmeier-Haack反应可轻松获得起始底物。从获得的甲醛中，通过Wittig反应合成了新的甲基，甲氧基和氰基取代的苯乙烯基噻吩并苯并双环[3.2.1]辛二烯衍生物，并进行了光化学环化，从而获得了新的环状结构。作为这项研究的一部分，还进行了起始2-取代的甲醛与丙酮的醛醇缩合反应，生成了噻吩稠合的苯并双环[3.2.1]辛二烯化合物，具有扩展的共轭作用。