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Synthesis and Rearrangement of Cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: an Access to Cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones by Ouro-Sama Adetchessi; Jean-Michel Léger; Jean Guillon; Isabelle Forfar-Bares; Jean-Jacques Bosc; Christian Jarry is a Chemistry article available to read on EtoBox.

What is Synthesis and Rearrangement of Cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: an Access to Cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones about?

2-Substituted-4a-hydroxy-9H-cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-9-ones 2a-c were synthesized by an one-step cyclocondensation from the 5-substituted-2-amino-2-oxazolines 1a-c with ethyl 2-oxocyclohexanecarboxylate in ethanol at room temperature, and easily dehydrated to provide 2-substituted-9H-cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-9-ones 3. In refluxing xylene, the reaction conducted with various ethyl 2-oxocycloalkanecarboxylates led to the two isomeric 2-substituted-8/9H-cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones 3 and 2-substituted-5H-cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones 4. The structure of some compounds was unambiguously established using X-ray crystallography. According to results from the DSC analysis of compound 2a, formation of the thermodynamically stable pyrimidinones 4 could be related to an intramolecular rearrangement of kinetically controlled pyrimidinones 3.

Who reads Synthesis and Rearrangement of Cycloalkyl[1,2-e]oxazolo[3,2-a]pyrimidin-8/9-ones: an Access to Cycloalkyl[1,2-d]oxazolo[3,2-a]pyrimidin-5-ones?

Author

Ouro-Sama Adetchessi; Jean-Michel Léger; Jean Guillon; Isabelle Forfar-Bares; Jean-Jacques Bosc; Christian Jarry

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)