Base‐Promoted Synthesis of Polysubstituted 4‐Aminoquinolines from Ynones and 2‐Aminobenzonitriles under Transition‐Metal‐Free Conditions. Issue 10 (9th March 2021)

• Record Type: Journal Article
• Authors: Kumar, Ankit; Mishra, Pawan K.; Saini, Kapil Mohan; Verma, Akhilesh K.
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 10(2021)
• Page Start: 2546
• Page End: 2551
• Publication Date: 2021-03-09
• Subjects: Aminoquinolines -- SNAr -- 2-Aminobenzonitrile -- Ynones -- Aza-Michael addition; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100023
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A transition‐metal‐free and base‐promoted one‐pot reaction of ynones with 2‐aminobenzonitriles is described. The reaction was initiated through sequential aza‐Michael addition/intramolecular annulation to afford various multisubstituted 4‐aminoquinolines and 4‐amino‐1, 8‐naphthyridines in good to excellent yields. Operational simplicity, high atom‐economy with broad substrate scope makes this protocol more attractive. Also, the gram‐scale synthesis and further transformation of the product were studied. Additionally, 2‐haloarylyones as substrate provide N‐arylquinolones as the sole product via the SN Ar mechanism. Abstract :