A one-pot approach to 10-(1H-1,2,3-triazol-11-yl)pyrimido[1,2-a]indoles via aryne-mediated transformations of 3-(pyrimidin-2-yl)-1,2,4-triazines

摘要

An efficient synthetic approach toward 10-(1H-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. (C) 2016 Elsevier Ltd. All rights reserved.