Gold(III)-catalyzed site-selective and divergent synthesis of 2-Aminopyrroles and Quinoline-based Polyazaheterocycles

• Verfasst von: Zeng, Zhongyi [VerfasserIn]
• Verfasst von: Jin, Hongming [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Gold(III)-catalyzed site-selective and divergent synthesis of 2-Aminopyrroles and Quinoline-based Polyazaheterocycles
• Verf.angabe: Zhongyi Zeng, Hongming Jin, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
• E-Jahr: 2018
• Jahr: December 10, 2018
• Umfang: 5 S.
• Fussnoten: Laut Frontdoor bereits am 11. Oktober 2018 erschienen ; Gesehen am 11.12.2018
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Ort Quelle: Weinheim : Wiley-VCH, 1962
• Jahr Quelle: 2018
• Band/Heft Quelle: 57(2018), 50, Seite 16549-16553
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201810369
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: aminopyrroles
• Sach-SW: anthranils
• Sach-SW: quinoline-embedded polyazaheterocycles
• Sach-SW: site-selective and divergent synthesis
• Sach-SW: α-imino gold carbenes
• K10plus-PPN: 1585055328

Abstract

A facile, site-selective, and divergent approach to construct 2-aminopyrroles and quinoline-fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one-pot strategy uses readily available starting materials, proceeds in a highly step- and atom-economical manner, with broad substrate scope and scale-up potential. The key element for success in this tandem reaction is a catalyst-directed preferred quenching of the in situ generated gold carbene intermediates by a nucleophilic benzyl/2-furylmethyl moiety on the ynamides as an alternative to the known C−H annulation leading to indoles.