A one-pot approach to 10-(1H-1, 2, 3-triazol-1-yl)pyrimido[1, 2-a]indoles via aryne-mediated transformations of 3-(pyrimidin-2-yl)-1, 2, 4-triazines. Issue 34 (24th August 2016)

• Record Type: Journal Article
• Authors: Kopchuk, Dmitry S.; Chepchugov, Nikolay V.; Khasanov, Albert F.; Kovalev, Igor S.; Santra, Sougata; Nosova, Emiliya V.; Zyryanov, Grigory V.; Majee, Adinath; Rusinov, Vladimir L.; Chupakhin, Oleg N.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 34(2016)
• Page Start: 3862
• Page End: 3865
• Publication Date: 2016-08-24
• Subjects: 1, 2, 4-Triazines -- 1, 2-Dehydrobenzene -- 4, 5-Difluoro-1, 2-dehydrobenzene -- Transformations -- 10-(1H-1, 2, 3-Triazol-1-yl)pyrimido[1, 2-a]indoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.07.052
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An efficient synthetic approach to 10-(1 H -1, 2, 3-triazol-1-yl)pyrimido[1, 2- a ]indoles was developed. Only readily available reagents, simple procedures, and short reaction times were used. Difluoro-benzyne results in the corresponding 2, 3-difluoro-pyrimido[1, 2- a ]indoles. This procedure will open up new routes for the synthesis of pyrimido[1, 2- a ]indoles. Abstract: An efficient synthetic approach toward 10-(1 H -1, 2, 3-triazol-1-yl)pyrimido[1, 2- a ]indoles, including fluorinated derivatives, has been developed. The transformation of the 1, 2, 4-triazine ring of readily available 3-(pyrimidin-2-yl)-1, 2, 4-triazines proceeds via reaction with in situ generated aryne intermediates. Improved methods have been developed for the synthesis of the starting 5, 6-diaryl- and 6-aryl-3-(pyrimidin-2-yl)-1, 2, 4-triazines. The influence that the nature of the aryne intermediate has on the reaction pathway was studied. The structure of the obtained pyrimido[1, 2- a ]indoles was confirmed by single crystal X-ray crystallography.