Synthesis of 1, 8-naphthyridines from 2-aminonicotinaldehydes and terminal alkynes. Issue 18 (4th May 2016)

• Record Type: Journal Article
• Authors: Li, Binbin; Nguyen, Steven; Huang, Jianjun; Wang, Gaigai; Wei, Huiping; Pereshivko, Olga P.; Peshkov, Vsevolod A.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 18(2016)
• Page Start: 1958
• Page End: 1962
• Publication Date: 2016-05-04
• Subjects: 1, 8-Naphthyridines -- 2-Aminonicotinaldehydes -- Alkynes -- Copper catalysis -- Hydroamination -- Friedländer synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.070
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 1, 8-Naphthyridine core can be assembled from 2-aminonicotinaldehydes and terminal alkynes. The developed procedure utilizes copper(II) triflate catalyst in the presence of diethylamine. The developed procedure selectively yields 3-substituted 1, 8-naphthyridines. Abstract: A copper(II) triflate-catalyzed diethylamine-assisted protocol for the reaction of 2-aminonicotinaldehydes and terminal alkynes leading to 1, 8-naphthyridines is described. The overall process presumably involves a copper(II) triflate-catalyzed hydroamination of the triple bond followed by the Friedländer-type condensation of the resulting enamine with 2-aminonicotinaldehyde.