Γ‐Functionalization of α, β‐Unsaturated Nitriles under Mild Conditions: Versatile Synthesis of 4‐Aryl‐2‐Bromopyridines. Issue 23 (7th October 2019)

• Record Type: Journal Article
• Authors: Sim, Jaeuk; Viji, Mayavan; Rhee, Jeongtae; Jo, Hyeju; Cho, Suk Joon; Park, Yunjeong; Seo, Seung‐Yong; Jung, Kwan‐Young; Lee, Heesoon; Jung, Jae‐Kyung
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 23(2019)
• Page Start: 5458
• Page End: 5465
• Publication Date: 2019-10-07
• Subjects: γ-functionalization -- 2-halopyridine -- α-pyrone -- α, β-unsaturated nitrile -- vinylogus enaminonitrile; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901002
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: This report describes the synthesis of 4‐aryl‐2‐halopyridines via γ ‐functionalization of α, β ‐unsaturated nitriles, which were obtained by the HWE reaction with the corresponding ketones. The key features of our methods involve a conjugated γ‐ enamine formation of α, β ‐unsaturated nitrile (enamino nitrile), followed by consecutive intramolecular cyclization, resulting in heteroaromatic compounds like 2‐halopyridines, α ‐pyrone, etc. Abstract :