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Pyridazines. XXV . Formation of 2‐benzoyl‐2,5‐dihydro‐3‐pyridazinecarbonitrile derivatives in the reissert reaction of pyridazines
Author(s) -
Dostal Wolfgang,
Heinisch Gottfried
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220615
Subject(s) - chemistry , benzoyl chloride , pyridazine , cyanide ion , potassium cyanide , cyanide , medicinal chemistry , chloride , potassium , solvent , organic chemistry
Pyridazines 1a, b on treatment with potassium cyanide/benzoyl chloride in a mixed solvent system gave 2‐benzoyl‐2,5‐dihydro‐3‐pyridazinecarbonitriles 3a, b together with products resulting from attack of one mole of cyanide ion and three moles of benzoyl chloride ( 5a, b ). The structures of these novel compounds are proved. A plausible reaction mechanism is proposed, involving rearrangement of initially formed 2a, b into 3a, b . Furthermore, the synthesis of the pyridazine Reissert compound 2a is reported.