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Pregled bibliografske jedinice broj: 601826

Synthesis and Structural Elucidation of Diversely Functionalized 5, 10-Diaza[5]Helicenes


Waghray, Deepali; Zhang, Jing; Jacobs, Jeroen; Nulens, Wienand; Basarić, Nikola; Van Meervelt, Luc; Dehaen, Wim
Synthesis and Structural Elucidation of Diversely Functionalized 5, 10-Diaza[5]Helicenes // Journal of organic chemistry, 77 (2012), 22; 10176-10183 doi:10.1021/jo301814m (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis and Structural Elucidation of Diversely Functionalized 5, 10-Diaza[5]Helicenes

Autori
Waghray, Deepali ; Zhang, Jing ; Jacobs, Jeroen ; Nulens, Wienand ; Basarić, Nikola ; Van Meervelt, Luc ; Dehaen, Wim

Izvornik
Journal of organic chemistry (0022-3263) 77 (2012), 22; 10176-10183

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

Ključne riječi
Diaza[5]helicenes; Wittig reaction; photochemical electrocyclization

Sažetak
Diversely functionalized diaza[5]helicenes have been synthesized starting from 6, 9-dichloro-5, 10-diaza[5]helicene, which was prepared from a readily available quinoline building block via Wittig reaction followed by photochemical electrocyclization. The helicene skeleton was substituted by a variety of O-, S-, N-, and C- centered nucleophiles using nucleophilic aromatic substitution reactions and palladium-catalyzed reactions like Suzuki coupling and Buchwald −Hartwig aminations. We have determined, using X- ray single-crystal diffraction, the crystal structures of the chloro- and methoxysubstituted diaza[5]helicenes. A resolution strategy based on diastereomeric separation by substitution of the dichloro derivative with a chiral amine has been shown.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Autor s matičnim brojem:
Nikola Basarić, (250000)

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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