The preparation of 1H-pyrazole-1-carboxylic acid, 1,1-dimethylethyl esters from dilithiated C(alpha),N-hydrazones of hydrazinecarboxylic acid, 1,1-dimethylethyl ester

C(alpha),N-Hydrazones of hydrazinecarboxylic acid, 1,1-dimethylethyl ester [C(alpha),N-carbo-t-butoxyhydrazones] were metalated with excess lithium diisopropylamide, and the dianion-type intermediates were condensed with select aromatic esters followed by acid cyclization to substituted 1H-pyrazole-...

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Bibliographic Details
Published inSynthetic communications Vol. 26; no. 19; pp. 3659 - 3669
Main Authors Church, AC, Koller, MU, Hines, MA, Beam, CF
Format Journal Article
LanguageEnglish
Published NEW YORK Marcel Dekker Inc 01.10.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,4-DIANION
PHENYLHYDRAZONES
OXIMES
C(ALPHA),N-DILITHIOCARBOALKOXYHYDRAZONES
CONDENSATION
ALPHA
C(ALPHA)-DIANIONS
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Summary:C(alpha),N-Hydrazones of hydrazinecarboxylic acid, 1,1-dimethylethyl ester [C(alpha),N-carbo-t-butoxyhydrazones] were metalated with excess lithium diisopropylamide, and the dianion-type intermediates were condensed with select aromatic esters followed by acid cyclization to substituted 1H-pyrazole-1-carboxylic acid, 1,1-dimethylethyl esters (N-carbo-t-butoxypyrazoles).
ISSN:0039-7911
DOI:10.1080/00397919608003780