Novel synthesis of perfluoroalkylated indolizinylphosphonates via a DIPEA-promoted one-pot process

• Published in: Tetrahedron Vol. 74; no. 1; pp. 135 - 141
• Main Authors: Liu, Hao, He, Dong, Sun, Zhenhua, He, Weimin, Han, Jing, Chen, Jie, Deng, Hongmei, Shao, Min, Zhang, Hui, Cao, Weiguo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.01.2018; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Indolizine; Multicomponent reaction; One-pot synthesis; Perfluoroalkynylphosphonate; Physical Sciences; Science & Technology; One-pot synthesis; Multicomponent reaction; Indolizine; Perfluoroalkynylphosphonate; ANTIVIRAL AGENTS; CATALYSIS; INDOLIZINES; ANNULATION; ANALOGS; PYRIDINIUM YLIDES; 1,3-DIPOLAR CYCLOADDITION; PHOSPHONATE HYBRID MATERIALS; INSIGHTS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2017.11.050

DIPEA-promoted one-pot synthesis of perfluoroalkylated indolizinylphosphonates by the reaction of pyridines 1, bromomethyl ketones 2 with perfluoroalkynylphosphonates 3 is described. This procedure is compatible with a broad range of functional groups in both pyridines and ketones with good yields. The reaction proceeds through a tandem CN bond formation followed by an intramolecular cyclization. DIPEA-promoted one-pot synthesis of perfluoroalkylated indolizinylphosphonates by the reaction of pyridines 1, bromomethyl ketones 2 with perfluoproalkynylphosphonates 3 is described. This procedure is compatible with a broad range of functional groups in both pyridines and ketones with good yields. The reaction proceeds through a tandem CN bond formation followed by an intramolecular cyclization. [Display omitted]