A Simple Green Protocol for the Condensation of Anthranilic Hydrazide with Cyclohexanone and N-Benzylpiperidinone in Water

An environmentally benign condensation of anthranilic hydrazide with cyclohexanone or N‐benzylpiperidin‐4‐one in aqueous medium has been developed for the synthesis of benzoylhydrazones A. The thermal rearrangements of hydrazones A yielded 3′‐aminospiro‐quinazolinones B. When A or B was reacted repe...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 53; no. 1; pp. 32 - 37
Main Authors Miklos, Ferenc, Fueloep, Ferenc
Format Journal Article
LanguageEnglish
Published HOBOKEN Blackwell Publishing Ltd 01.01.2016
Wiley
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Condensation
Hogs
Physical Sciences
Science & Technology
KETONES
ACID
SERIES
HETEROCYCLES
ONE-POT
CHEMISTRY
INHIBITORS
ANTITHROMBOTIC AGENTS M58163
DYNAMIC KINETIC RESOLUTION
1-ARYLSULFONYL-3-PIPERAZINONE DERIVATIVES
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Summary:An environmentally benign condensation of anthranilic hydrazide with cyclohexanone or N‐benzylpiperidin‐4‐one in aqueous medium has been developed for the synthesis of benzoylhydrazones A. The thermal rearrangements of hydrazones A yielded 3′‐aminospiro‐quinazolinones B. When A or B was reacted repeatedly with cyclohexanone or N‐benzylpiperidin‐4‐one, spiroquinazoline‐hydrazones C were formed. From aqueous suspensions, products could be isolated in high purity by simple filtration.
Bibliography:istex:BAE366E34C2386DC241DCEEFCB05D5ED661B3111
ArticleID:JHET1844
ark:/67375/WNG-6RF7RHNQ-8
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1844