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DOI: 10.1055/a-2529-5234
A Novel Condensation–Cyclization Reaction of 4-Chloro-3-formylcoumarin with Amidoximes: Facile Synthesis of Coumarin-Fused Pyrimidinones
The Institute for Advanced Studies in Basic Sciences is thanked for partial supporting this work. This work was based upon research funded by the Iran National Science Foundation (INSF) under project no. 4038081.

Abstract
Coumarin-fused heterocyclic compounds are important materials with wide applications in biological and drug design. We report here a novel condensation–cyclization reaction of 4-chloro-3-formylcoumarin with amidoximes. The reaction gave a novel conjunction and hybrid compound of coumarin with pyrimidinones. Condensation–cyclization reactions of amidoximes with 4-chloro-3-formylcoumarin under catalyst-free conditions gave various coumarin derivatives of pyrimidinones in good to excellent yield.
Key words
coumarins - amidoximes - condensation–cyclization - pyrimidines - 4-chloro-3-formylcoumarinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a- 2529-5234.
- Supporting Information
Publikationsverlauf
Eingereicht: 30. Dezember 2024
Angenommen nach Revision: 30. Januar 2025
Accepted Manuscript online:
30. Januar 2025
Artikel online veröffentlicht:
14. März 2025
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References and Notes
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- 27 General Procedure for the Condensation Cyclization Reaction of Amidoxime 1 with 4-Chloro-3-formylcoumarin (2) Amidoxime 1 (1 mmol) was added to a solution of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde (2, 1 mmol) in DMF (2 mL). The reaction mixture stirred at 80 °C for 2 h and then cooled to room temperature. Ice-water (3 mL) was added to the reaction mixture, and the formed solid was filtrated. The obtained solid was washed with ethyl acetate (3 × 2 mL) and dried on air. All products are pure and gave satisfactory spectral data in accordance with the assigned structures (see the Supporting Information). 2-Phenyl-3H-chromeno[4,3-d]pyrimidine-4,5-dione (3a) Yellow solid (94%, 270 mg, 237–239 °C). 1H NMR (400 MHz, DMSO-d 6): δ = 9.15 (s, 1 H), 8.66–8.62 (m, 2 H), 8.49 (dd, J = 8.0, 1.7 Hz, 1 H), 7.78 (ddd, J = 8.6, 7.3, 1.6 Hz, 1 H), 7.74–7.68 (m, 1 H), 7.67–7.61 (m, 2 H), 7.56 (dtd, J = 8.1, 3.6, 1.1 Hz, 2 H).13C{1H} NMR (101 MHz, DMSO-d 6): δ = 159.5, 157.9, 152.9, 146.0, 144.2, 133.9, 132.8, 131.3, 130.9, 128.6, 125.9, 124.8, 117.8, 117.7, 115.4. HRMS (ESI): m/z calcd for C17H10N2O3Na [M + Na]: 313.0589; found: 313.0587.
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