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Synthesis of α‐Cyanoenamines by Cyanation of α‐Bromoimmonium Bromides and Dehydrobromination of β‐bromo‐α‐(dialkylamino)nitriles
Author(s) -
De Kimpe Norbert,
Verhé Roland,
De Buyck Laurent,
Schamp Niceas
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831161208
Subject(s) - chemistry , cyanation , potassium cyanide , dimethylformamide , organic chemistry , cyanide , nitrile , potassium , medicinal chemistry , catalysis , solvent
The reaction of α‐bromoimmonium bromides 4 with potassium cyanide in dimethylformamide gave rise to β‐bromo‐α‐(dialkylamino)nitriles 5 , which were dehydrobrominated in various basesolvent systems to afford ( E )‐ and ( Z )‐α‐cyanoenamines 2 . An adaption of a previously published preparation of α‐cyanoenamines starting from aldehydes via enamines led to an improved, efficient and fast synthesis of the title compounds.