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6‐(substituted phenyl)‐5‐methyl‐4,5‐dihydro‐pyridazin‐3(2 H )‐ones of medicinal interest. The synthesis of SK&F 94836 and SK&F 95654
Author(s) -
Burpitt B. E.,
Crawford L. P.,
Davies B. J.,
Mistry J.,
Mitchell M. B.,
Pancholi K. D.,
Coates W. J.
Publication year - 1988
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.5570250615
Subject(s) - chemistry , substituent , solvent , medicinal chemistry , 2 pyridone , stereochemistry , combinatorial chemistry , organic chemistry
Two synthetic routes to the dihydropyridazinone‐cyanoguanidine 4 (SK&F 94836) are described, both proceeding via the anilino compound 6. An efficient synthesis of the dihydropyridazinone‐pyridone 5 (SK&F 95654) is reported. This synthesis proceeds via the fluoro‐keto‐acid 24 , with subsequent displacement of the fluoro substituent by 4‐pyridone. The surprising effectiveness of water as a solvent in this reaction has been highlighted.