Mechanism[ edit ] The reaction of bromine with sodium hydroxide forms sodium hypobromite in situ , which transforms the primary amide into an intermediate isocyanate. The formation of an intermediate nitrene is not possible because it implies also the formation of a hydroxamic acid as a byproduct, which has never been observed. The intermediate isocyanate is hydrolyzed to a primary amine, giving off carbon dioxide. Base abstraction of the remaining amide proton gives a bromoamide anion. The bromoamide anion rearranges as the R group attached to the carbonyl carbon migrates to nitrogen at the same time the bromide ion leaves, giving an isocyanate.

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Hofmann rearrangement

This article has been cited by other articles in PMC. Abstract Schiff bases 9a-l of 3-amino-6,8-dibromophenyl-quinazolin 3H -ones 8 with various substituted aldehydes were obtained by refluxing molar equivalents of the reactants in dry ethanol for 6 h. The aminoquinazoline 8 was inturn obtained from 3,5-dibromoantharlinic acid via intermediate 7. All the synthesized compounds 9a-l were evaluated for their anticonvulsant activity on albino mice by maximal electroshock method using phenytoin as a standard. The compound 9l bearing a cinnamyl function displays a very high activity Keywords: Anticonvulsant, maximal electroshock method, Schiff base, Quinazolin 3H -one, 3-aminoquinazolines Quinazolinones and their Schiff bases are an important class of heterocyclic systems, enjoying considerable interest on account of their diverse range of biological activities[ 1 — 9 ] such as antimicrobial, analgesic and antiinflammatory, anticonvulsant, anticancer, antitubercular, antimalarial, antiviral, antihelmintic and, in particular, very high anticonvulsant activity.


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