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

Vuk, Dragana; Škorić, Irena; Milašinović, Valentina; Molčanov, Krešimir; Marinić, Željko (2020) A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes. Beilstein Journal of Organic Chemistry, 16 . pp. 1092-1099. ISSN 1860-5397

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In order to prepare novel polycyclic derivatives of bicyclo[3.2.1]octadiene systems fused with thiophene ring, photochemical cyclizations and aldol condensation were carried out. The starting substrates were easily obtained by Vilsmeier-Haack’s reaction of bicyclo[3.2.1]octadiene thiophene derivatives From the obtained carbaldehydes, novel methyl-, methoxy- and cyano-substituted styryl thieno- benzobicyclo[3.2.1]octadiene derivatives were formed by Wittig's reaction and subjected to photochemical reactions, in terms of obtaining new annulated structures. As a part of this study, aldol reaction of starting 2-substituted carbaldehyde and acetone was also performed, which produced the thieno-fused benzobicyclo[3.2.1]octadiene compound with an extended conjugation.

Item Type: Article
Uncontrolled Keywords: bicyclo[3.2.1]octadiene ; photocyclization ; thiophene ; Vilsmeier-Haack’s reaction ; Wittig reaction
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
NMR Center
Depositing User: Krešimir Molčanov
Date Deposited: 08 Jul 2020 08:04
DOI: 10.3762/bjoc.16.96

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