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Formation of Polycyclic Skeletons by Photochemical Transformations of Pyridyl‐ and Thienylbutadiene Derivatives
Author(s) -
Šagud Ivana,
Levačić Marko,
Marinić Željko,
Škorić Irena
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700481
Subject(s) - chemistry , wittig reaction , intramolecular force , cycloaddition , thiophene , pyridine , conjugated system , electrocyclic reaction , 1,3 butadiene , medicinal chemistry , photochemistry , organic chemistry , bicyclic molecule , catalysis , polymer
In order to study the influence of heterocyclic nuclei on the photochemical behavior of conjugated butadiene systems, novel butadiene derivatives E , Z ‐ and E , E ‐2/3‐[4‐(2‐vinylphenyl)buta‐1,3‐dienyl]thiophene as well as E , Z ‐ and E , E ‐3/4‐[4‐(2‐vinylphenyl)buta‐1,3‐dienyl]pyridine have been synthesized. The Wittig reaction was utilized in a two‐step reaction course. During the first Wittig reaction, the corresponding aldehydes, namely 2/3‐thiophenecarboxaldehyde and 3/4‐pyridinecarboxaldehyde, reacted with formylmethylenetriphenylphosphorane to give the corresponding acrylaldehydes, which reacted with the diphosphonium salt of α,α′‐ o ‐xylenedibromide in the second Wittig reaction to give new butadiene derivatives. These butadiene derivatives afforded, by photochemical intramolecular cycloaddition, new fused tricyclic as well as tetracyclic derivatives. For the first time, a study of efficiency was conducted where the efficiency of intramolecular cycloaddition of these heterocyclic butadiene derivatives was investigated by simultaneous use of ferrioxalate and valerophenone actinometers.