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Synthesis 2016; 48(07): 1029-1045
DOI: 10.1055/s-0035-1561287
DOI: 10.1055/s-0035-1561287
paper
Synthesis of Fluorescent 2-Substituted 6-(Het)aryl-7-deazapurine Bases {4-(Het)aryl-pyrrolo[2,3-d]pyrimidines} by Aqueous Suzuki–Miyaura Cross-Coupling Reactions
Further Information
Publication History
Received: 16 November 2015
Accepted after revision: 20 November 2015
Publication Date:
11 January 2016 (online)
Abstract
A series of 4-(het)aryl-pyrrolo[2,3-d]pyrimidines [6-(het)aryl-7-deazapurine bases] bearing a H, NH2, CH3, F, or Cl group at the 2-position and either H or F at the 5-position (position 7 of 7-deazapurine) were prepared in a single step by the aqueous Suzuki–Miyaura cross-coupling reactions of the corresponding 6-chloro-7-deazapurines with (het)arylboronic acids. Unlike their ribonucleoside derivatives, which are potent cytostatics, the deazapurine bases did not show significant biological activity but most of them exerted bright fluorescence with emission maxima 368–468 nm and high quantum yields up to 0.83.
Key words
nucleobases - deazapurines - pyrrolo[2,3-d]pyrimidines - Suzuki cross-coupling - arylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561287.
- Supporting Information
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