3‐Alkenyltyrosines Accessed by Suzuki–Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions. Issue 7 (1st June 2017)

• Record Type: Journal Article
• Authors: Vasconcelos, Stanley N. S.; Menezes da Silva, Vitor H.; Braga, Ataualpa A. C.; Shamim, Anwar; Souza, Frederico B.; Pimenta, Daniel C.; Stefani, Hélio A.
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 7(2017)
• Page Start: 913
• Page End: 920
• Publication Date: 2017-06-01
• Subjects: mechanistic investigations -- multicomponent reactions -- quinoline -- stilbene -- tyrosine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700154
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 3‐Vinyl and 3‐stilbenyl tyrosine derivatives, accessed by the Suzuki–Miyaura coupling reaction in good yields, are presented. These synthetic olefins then provided a fast and effective synthesis of functionalized quinolines by a silver‐catalyzed, microwave‐mediated Povarov reaction in just 40 min. In addition, we demonstrate a tandem one‐pot microwave‐mediated Povarov–CuAAC (copper‐catalyzed azide–alkyne cycloaddition) synthesis to provide a 1, 2, 3‐triazole ring with 35 % overall yield. We propose a Povarov/aromatization mechanism, based on high‐resolution mass spectrometry experiments, combined with computational studies based on density functional theory (DFT) methods. Abstract : Fast functionalized quinolines : An unprecedented synthesis of 4‐tyrosilquinoline‐2‐carboxylates by a silver catalyzed, microwave‐mediated Povarov reaction from a Suzuki–Miyaura cross‐coupling product is reported. A plausible Povarov/aromatization mechanism is proposed, based on high‐resolution mass spectrometry experiments, combined with computational studies based on density functional theory (DFT) methods.