Synthesis of 2, 3, 6-trisubstituted pyridines by transition-metal free cyclization of 1, 3-diynes with amino acids. Issue 31 (2nd August 2017)

• Record Type: Journal Article
• Authors: Zhou, Gang; Zhao, Xiaoming; Dan, Wenyan
• Is Part Of: Tetrahedron letters. Volume 58:Issue 31(2017)
• Page Start: 3085
• Page End: 3088
• Publication Date: 2017-08-02
• Subjects: Amino acid -- 1, 3-Diyne -- Cyclization -- Pyridine -- Transition-metal free; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.080
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of pyridines from 1, 3-diynes and amino acid was presented. 3-Aminopropanoic acid provided the desired products. 4-Aminobutanoic acid provided 2-(3, 6-diphenylpyridin-2-yl)acetic acid. Glycine afforded 2, 5-diphenylpyridine. Abstract: Amino acids are firstly employed in transition-metal free heterocyclization reaction of 1, 3-diynes in the presence of K3 PO4 and DMSO at 120 °C. This method produces 2, 3, 6-trisubstituted pyridines with up to 86% yield. The –CO2 H group on the amino acids is crucial for this heterocyclization reaction. The mechanism of such a heterocyclization reaction is discussed, as well.