Jump to main content
Jump to site search

Issue 48, 2018
Previous Article Next Article

An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

Author affiliations

Abstract

A convenient synthesis of 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones (DTPs) from 3,3-diamino-2-(arylazo)acrylonitriles through a versatile and readily accessible two-step procedure is described. Density functional theory (DFT) calculations were performed to explain the selectivity of the heterocyclization step, which predominantly afforded 6-amino-5-(arylazo)pyrimidin-2(1H)-thiones in chloroform or ethanol, and 2,3-dihydro-1,2,4-triazines in toluene or DMF. Novel 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones were obtained in good yields and showed absorption in the ultraviolet region and good emission in the blue region. The photophysical properties of DTPs were better than those cited in select literature examples of 8-azapurines. Owing to the facile synthesis and good photophysical characteristics in an aqueous medium, the new DTPs should have potential applications as organic fluorophores in fluorescence imaging and materials science.

Graphical abstract: An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Oct 2018, accepted on 22 Nov 2018 and first published on 23 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02644K
Citation: Org. Biomol. Chem., 2018,16, 9420-9429
  •   Request permissions

    An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

    A. K. Eltyshev, P. O. Suntsova, K. D. Karmatskaia, O. S. Taniya, P. A. Slepukhin, E. Benassi and N. P. Belskaya, Org. Biomol. Chem., 2018, 16, 9420
    DOI: 10.1039/C8OB02644K

Search articles by author

Spotlight

Advertisements