Abstract
Two series of 2H-pyrano[2,3-d]pyrimidine-2,5(6H)-dione derivatives have been prepared. Thus, the reaction of 6-hydroxy-pyrimidin-4(3H)-ones (1 a–c) with bis-2,4,6-trichlorphenyl malonates (2 a–d) or diethyl malonates (3 a–d) afforded good yields of 4-hydroxy-2H-pyrano[2,3-d]pyrimidine-2,5(6H)-diones (4 a-l). Application of our modifiedPechmann reaction9–11 using β-aminocrotonate (5) or β-keto esters (6, 7) in the presence of ammonium acetate yielded the 2H-pyrano[2,3-d]pyrimidinediones8 a–h.
Zusammenfassung
Zwei Serien von 2H-Pyrano[2,3-d]pyrimidin-2,5(6H)-dionen wurden hergestellt. Die Reaktion der 6-Hydroxy-pyrimidin-4(3H)-one (1 a–c) mit Malonsäure-bis-2,4,6-trichlorphenylestern (2 a–d) oder Malonsäurediethylestern (3 a–d) lieferte 4-Hydroxy-2H-pyrano[2,3—d]pyrimidin-2,5(6H)-dione (4 a–l) in guten Ausbeuten. Die Anwendung unserer modifiziertenPechmann-Reaktion9–11 auf1 a–c, unter Verwendung des β-Aminocrotonsäureesters (5) oder der β-Ketoester6, 7 in Gegenwart von Ammonacetat, gab die 2H-Pyrano[2,3-d]pyrimidindione8 a–h.
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Dedicated to Prof. Dr.Karl Schlögl, University of Vienna, on the occasion of his 60th birthday.
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Habib, N.S., Kappe, T. Synthesis of 2H-pyrano[2,3-d]pyrimidine derivatives. Monatsh Chem 115, 1459–1466 (1984). https://doi.org/10.1007/BF00816345
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DOI: https://doi.org/10.1007/BF00816345