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Stereospecific synthesis of new 5‐substituted 6‐methyl‐4,5‐dihydro‐2 H ‐pyridazin‐3‐ones. X‐ray assignment study
Author(s) -
Taoufik J.,
Couquelet J. D.,
Couquelet J. M.,
Carpy A.
Publication year - 1984
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.5570210207
Subject(s) - chemistry , stereospecificity , hydrazine (antidepressant) , hydrate , ring (chemistry) , furan , diastereomer , stereochemistry , crystal structure , medicinal chemistry , crystallography , organic chemistry , catalysis , chromatography
Reaction of hydrazine hydrate with 4,5‐dihydro‐3 H ‐4‐acetyl furan‐2‐ones I led to ring opening and rearrangement into 6‐methyl‐4,5‐dihydro‐2 H ‐pyridazin‐3‐ones II ( 1–20 ), the structure of which was determined by spectroscopic methods (ir, 1 H and 13 C nmr). An X‐ray crystal structure study of compound 2 supports the assignment of configuration erythro (5 RS , 7 SR ) for pyridazinones II. Stereochemical courses of this new synthetic route are discussed.