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 | Zendy

Kappe C. Oliver | Zendy

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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

Author(s) -

Kappe C. Oliver

Publication year - 1990

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199019900196

Subject(s) - chemistry , sodium azide , azide , geminal , nitrile , decomposition , bromide , medicinal chemistry , organic chemistry

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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