Synthesis, Table of Contents Synthesis 2021; 53(07): 1237-1246DOI: 10.1055/s-0040-1706105 feature Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis Marian Blanco Ponce a Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany b University of Granma, Centre for Study of Applied Chemistry, Carretera Manzanillo Km 17½, 85100, Bayamo, Cuba , Silvio Parpart a Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany , Alexander Villinger a Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany , Eugenio Torres Rodríguez b University of Granma, Centre for Study of Applied Chemistry, Carretera Manzanillo Km 17½, 85100, Bayamo, Cuba , Peter Ehlers ∗ a Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany c Leibniz-Institute for Catalysis, A.-Einstein-Str. 29, 18059 Rostock, Germany , Peter Langer ∗ a Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany c Leibniz-Institute for Catalysis, A.-Einstein-Str. 29, 18059 Rostock, Germany › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds. Key words Key wordsacylation - alkyne-carbonyl metathesis - Brønsted acid - cyclization - pyrrolonaphthyridines Full Text References References 1a Schuter M, Blechert S. Angew. Chem., Int. Ed. Engl. 1997; 36: 2036 1b Chatterjee AK, Choi T.-L, Sanders DP, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360 1c Villar H, Frings M, Bolm C. Chem. Soc. Rev. 2007; 36: 55 1d van den Broek SA. M. W, Meeuwissen SA, van Delft FL, Rutjes FP. J. T. In Metathesis in Natural Products: Strategies, Substrates and Catalysts . Cossy J, Arseniyadis S, Meyer C. Wiley-VCH; Weinheim: 2010: 45-85 1e Ogba OM, Warner NC, O’Leary DJ, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510 1f Ehrhorn H, Tamm M. Chem. Eur. 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The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Supplementary Material Supplementary Material Supporting Information
