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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 .