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Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives


Alešković, Marija; Basarić, Nikola; Mlinarić-Majerski, Kata
Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives // Journal of heterocyclic chemistry, 48 (2011), 6; 1329-1335 doi:10.1002/jhet.792 (međunarodna recenzija, članak, znanstveni)


Naslov
Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives

Autori
Alešković, Marija ; Basarić, Nikola ; Mlinarić-Majerski, Kata

Izvornik
Journal of heterocyclic chemistry (0022-152X) 48 (2011), 6; 1329-1335

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

Ključne riječi
Synthesis of aminoarylpyrroles; Suzuki-Miyaura coupling; 2-(o-substituted aryl)pyrroles; Pd-catalyzed cross coupling

Sažetak
A facile three-step synthesis of 2-(2-aminophenyl)pyrrole (1) and 2-(2- aminomethylphenyl)pyrrole (2) is reported by use of Suzuki coupling of N-Boc-pyrrol-2-yl boronic acid (3) and o-substituted aryl halogenides, followed by hydrogenation. The Pdcatalyzed cross coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron-donating and electron-withdrawing substituents, 5a-g. Moreover, Pdcatalyzed coupling of o-bromoaniline and 3 could be applied for the one step preparation of pyrrolo[1, 2-c]quinazolin-5(6H)-one (8). Keywords: Synthesis of aminoarylpyrroles, Suzuki-Miyaura coupling, 2-(o-substituted aryl)pyrroles, Pd-catalyzed cross coupling

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

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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