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Synthesis 2019; 51(15): 2965-2976
DOI: 10.1055/s-0037-1612428
DOI: 10.1055/s-0037-1612428
paper
Synthesis and Photophysical Properties of 1,4-Dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins
The authors are thankful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Grant 429158/2018-1), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET, PUE IQUIR 2016).Further Information
Publication History
Received: 28 January 2019
Accepted after revision: 15 March 2019
Publication Date:
10 April 2019 (online)
Abstract
A facile protocol for the unprecedented one-pot H2SO4-mediated hydroxymethylation/cyclative N,O-acetalization of 4-aminocoumarins to 1,4-dihydro-2H,5H-chromeno[4,3-d][1,3]oxazin-5-ones, in moderate to good yields, was developed and optimized. The scope and limitations of the transformation, which takes place in water or water/THF mixtures, were also studied. The nitrogen atom of the resulting tricycles was used to tether alkyl, aryl and 1,2,3-triazolylmethyl moieties, employing a two-step click chemistry approach for the latter. The photophysical properties of the heterocycles, as well as of their 1,2,3-triazole derivatives, were also examined. The N-aryl derivatives exhibited high quantum yields of fluorescence (up to Φf = 0.69) and very large Stokes shifts (up to 201 nm).
Key words
4-aminocoumarins - tethered triazoles - 1,3-oxazines - cyclization reaction - photophysical propertiesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612428.
- Supporting Information
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