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DOI: 10.1055/a-2370-6760
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Microwave-Assisted Synthesis of Fluorescent 8-Aryl-7-deazaguanines

Hunter B. D. Cheney
b   Department of Chemistry and Biochemistry, University of Notre Dame, 236 Cavanaugh Dr, Notre Dame, IN 46556, USA
,
Elise S. Zevitz
a   Chemistry Department, University of Wisconsin Parkside, 900 Wood Road, Kenosha WI 53144, USA
,
Madeline G. Herbrechtsmeier
a   Chemistry Department, University of Wisconsin Parkside, 900 Wood Road, Kenosha WI 53144, USA
,
Ilirian Dhimitruka  ∗
a   Chemistry Department, University of Wisconsin Parkside, 900 Wood Road, Kenosha WI 53144, USA
› Author AffiliationsFunding was provided by the University of Wisconsin Parkside, the Office of the Provost, and the College of Natural and Health Sciences, the Office of the Dean through a generous start-up package to Dr. Dhimitruka.
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Abstract

Microwave-assisted conditions were adapted to our previously published synthesis of 8-aryl-7-deazaguanines via cyclocondensation of phenacyl bromides with 2,4-diamino-6-hydroxypyrimidine in refluxing 1,4-dioxane. Upon microwave irradiation at 150–225 °C, 8-aryl-7-deazaguanines were obtained in high yield above 90% and within 15–60 min, compared to the 24–72 h that are required under reflux conditions. Three new fluorescent 8-heteroaryl-7-deazaguanines were additionally produced and characterized confirming our hypothesis that compounds of this class typically exhibit fluorescence properties, regardless of the aryl substituent.

Key words

fluorescent - 7-deazaguanines - phenacyl bromides - 2,4-diamino-6-hydroxypyrimidine - microwave-assisted synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2370-6760.
  • Supporting Information


Publication History

Received: 11 June 2024

Accepted after revision: 22 July 2024

Accepted Manuscript online:
22 July 2024

Article published online:
13 August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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  • 19 Procedure 2 mmol of 2,4-diamino-6-hydroxypyrimidine, 2 mmol of substituted phenacyl bromide, 2 mmol of triethylamine, and 10 mL of 1,4-dioxane were charged in a 35 mL MW vial equipped with a stir bar. The vial was heated at the assigned reaction time (15–60 min) and temperature (150–225 °C). Upon cooling to room temperature, the reaction mixture was decanted, and 1,4-dioxane was carefully removed. The residual slurry was treated with 30 mL of water and stirred vigorously until a fine solid precipitated. The 1,4-dioxane phase was evaporated and treated with 15 mL of water until a fine solid precipitated. The combined solid product was filtered under vacuum, washed with 3 × 20 mL of water, and dried under vacuum. Subsequently, the isolated product was dried in an oven at 85 °C for a minimum of 8 h and was characterized via NMR spectroscopy and mass spectroscopy. Analytical samples of the isolated products were purified according to the following methods.
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