A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

Beilstein Journal of Organic Chemistry

Irena Škorić¹  Dragana Vuk¹  Krešimir Molčanov²  Valentina Milašinović²  Željko Marinić³ 

[1]Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia

[2]Division of Physical Chemistry, Rudjer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

[3]NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

关键词: bicyclo[3.2.1]octadiene;    photocyclization;    thiophene;    vilsmeier–haack reaction;    wittig reaction;   

DOI  :  10.3762/bjoc.16.96

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown