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The reactions of C(α), O ‐dilithiooximes, C(α), N ‐dilithiophenylhydrazones, and C(α), N,N ‐trilithiohydrazones with diethyl oxalate to give biisoxazoles, bipyrazoles, and pyridazones
Author(s) -
Sandifer Ronda M.,
Dasher Luther W.,
Hollinger Wayne M.,
Thomas C. Wayne,
Reames David C.,
Beam Charles F.,
Foote Robert S.,
Hauser Charles R.
Publication year - 1975
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.5570120614
Subject(s) - chemistry , oxalate , intramolecular force , medicinal chemistry , reaction mechanism , organic chemistry , catalysis
Several C (α), O ‐dilithiooximes were condensed with diethyl oxalate and acid‐cyclized to give biisoxazoles. Only dilithio p ‐fluoroacetophenone phenylhydrazone gave the bipyrazole when condensed with this diester. Other C(α), N ‐dilithiophenylhydrazones and several C(α), N,N ‐trilithio‐hydrazones were condensed with diethyl oxalate and acid‐cyclized to give the intramolecular 4‐hydroxy‐3‐pyridazones. Several non‐cyclized intermediates were isolated and a reaction mechanism is presented.