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Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o- vinylstyryl)oxazoles


Šagud, Ivana; Božić, Simona; Marinić, Željko; Šindler-Kulyk, Marija
Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o- vinylstyryl)oxazoles // Beilstein journal of organic chemistry, 10 (2014), 2222-2229 doi:10.3762/bjoc.10.230 (međunarodna recenzija, članak, znanstveni)


Naslov
Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o- vinylstyryl)oxazoles

Autori
Šagud, Ivana ; Božić, Simona ; Marinić, Željko ; Šindler-Kulyk, Marija

Izvornik
Beilstein journal of organic chemistry (1860-5397) 10 (2014); 2222-2229

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Bicyclo[3.2.1]octane; intramolecular photocycloaddition; oxazole; styryl; vinyl

Sažetak
Novel cis/trans-4- and cis/trans-5-(2- vinylstyryl)oxazoles have been synthesized by Wittig reactions from the diphosphonium salt of α, α’-o-xylene dibromide, formaldehyde and 4- and 5-oxazolecarbaldehydes, respectively. In contrast, trans-5-(2- vinylstyryl)oxazole has been synthesized by the van Leusen reaction from trans-3-(2-vinylphenyl)acrylaldehyde which is prepared from o-vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The 4- and 5-(2-vinylstyryl)oxazoles afford, by photochemical intramolecular cycloaddition, diverse fused oxazoline- benzobicyclo[3.2.1]octadienes, which are identified and characterized by spectroscopic methods. The photoproducts formed are relatively unstable and spontaneously or on silica gel undergo oxazoline ring opening followed by formation of formiato- or formamido-benzobicyclo[3.2.1]octenone derivatives. On irradiation of 4-(2- vinylstyryl)oxazole small quantities of electrocyclization product, 4-(1, 2- dihydronaphthalen-2-yl)oxazole, are isolated and spectroscopically characterized.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
125-0982933-2926 - Heteropolicikli, strukturne osnove za bioaktivne spojeve. Sinteza i fotokemija (Irena Škorić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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