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 | Zendy

Sandifer Ronda M. | Zendy; Dasher Luther W. | Zendy; Hollinger Wayne M. | Zendy; Thomas C. Wayne | Zendy; Reames David C. | Zendy; Beam Charles F. | Zendy; Foote Robert S. | Zendy; Hauser Charles R. | Zendy

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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.

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