Alkoxy base-mediated selective synthesis and new rearrangements of 1, 2, 4-triazolodipyrimidinones. Issue 8 (22nd February 2017)

• Record Type: Journal Article
• Authors: Pyatakov, Dmitry A.; Astakhov, Alexander V.; Sokolov, Andrey N.; Fakhrutdinov, Artem N.; Fitch, Andrew N.; Rybakov, Victor B.; Chernyshev, Vladimir V.; Chernyshev, Victor M.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 8(2017)
• Page Start: 748
• Page End: 754
• Publication Date: 2017-02-22
• Subjects: Nitrogen heterocycles -- Fused-ring systems -- Rearrangement -- 1, 2, 4-Triazolo[1, 5-a]pyrimidine -- Cascade reactions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.01.030
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Selective base-mediated cyclization of enaminoesters into triazolodipyrimidinones. A new cascade rearrangement of the triazolodipyrimidinones. An experimental and DFT study. Abstract: A versatile approach for the synthesis of [1, 2, 4]triazolodipyrimidinones with various annulations of the triazole and pyrimidine rings was developed. The isomeric triazolodipyrimidinones were obtained by the stepwise condensation of partially hydrogenated [1, 2, 4]triazolo[1, 5- a ]pyrimidin-2-amines with β-ketoesters or diethyl ethoxymethylenemalonate, alkoxy base-mediated cyclization of the enamines, and subsequent cascade rearrangement of the 10-oxo-[1, 2, 4]triazolo[1, 5- a :4, 3- a ′]dipyrimidines.