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An easy route to 2-substituted-2,3-dihydro-5(7)H-oxazolo[3,2-a]pyrimidin-5-ones and 7-ones starting from the corresponding 2-amino-2-oxazolines

✍ Scribed by I. Forfar; J. Guillon; S. Massip; J.-M. Léger; C. Jarry; J.-P. Fayet

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 56 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380403

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✦ Synopsis

Abstract

The isomeric 2‐substituted‐7(5)‐methyl‐2,3‐dihydro‐5(7)H‐oxazolo[3,2‐a]pyrimidin‐5‐ones 3a‐b and 7‐ones 2a‐b,7a were synthesized by cyclocondensation from the 5‐substituted‐2‐amino‐2‐oxazolines 1a‐b with biselectrophiles. In boiling ethanol, the reaction of 1a‐b with acetylenic esters led to a mixture of 2a‐b,7a with a small amount of (E)‐2‐N‐(2‐ethoxycarbonylethylene)‐5‐substituted‐2‐iminooxazolines 5a‐b. The ring annulation between 1a‐b and diketene gave the 2‐substituted‐7‐hydroxy‐7‐methyl‐2,3,6,7‐tetrahydro‐5__H__‐oxazolo[3,2‐a]pyrimidin‐5‐ones 4a‐b which can be easily dehydrated to provide the 2‐substituted‐7‐methyl‐2,3‐dihydro‐5__H__‐oxazolo[3,2‐a]pyrimidin‐5‐ones 3a‐b.

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