✦ LIBER ✦

Synthesis and reactions of biginelli compounds, 3. Unexpected formation of nitriles from reactions of 6-(dibromomethyl)-1,2,3,4-tetrahydro-2-oxo-5-pyrimidinecarboxylates with sodium azide

✍ Scribed by Kappe, C. Oliver

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 326 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199019900196

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✦ Synopsis

Abstract

The action of sodium azide on (dibromomethyl)pyrimidines 2a and 8a leads to the nitriles 3a and 9, whereas the 1‐methyl derivatives 2b and 8b afford the geminal diazides 7 and 10. The nitriles 3a, b add another mole of azide to give the tetrazoles 4a, b. The palladium‐catalyzed decomposition of azide 5, obtained from bromide 6 by treatment with sodium azide, yields nitrile 3a.

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