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Formation of Pyrazoles and of Imidazoles from Phenacyl Ketal Hydrazones of Aldehydes

✍ Scribed by David Scarpetti†; Kunio Kano††; Jean-Pierre Anselme


Book ID
101761173
Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
376 KB
Volume
95
Category
Article
ISSN
0037-9646

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✦ Synopsis


The cyclization of phenacyl ethylene ketal (pok) hydrazones of glyoxals, benzaldehyde and acetaldehyde to the pyrazoles is described, in the case of the hydrazones of benzaldehyde and acetaldehyde, the corresponding imidazoles are also formed. A mechanism is suggested for the formation of the imidazoles. We recently reported the novel cyclization of phenacyl ethylene ketal hydrazones of arylglyorals (1) to the corresponding 3-aroyl-4-phenyl-1-methylpyrazoles (2) .l The mechanism suggested earlisr' for this cyclization indicated that this process might serve as a general h e 1 h e 4 -3 -2 a ) Ar = C6E5 b) Ar = p-CE3C6E4 c) At = p-BrC6E4 to pyrazoles from suitably constructed aldehyde hydrazones of type and 5 . We now describe Benzene *lC13 -'U + 'tyR h e I he Me 5 s 7 a ) R = Ph, b) R = CE3 fully the results of this investigation and the unusual formation of imidazoles (1) as cogroducts of this reaction. The required I-methyl-1-pekhydrazones (I)' were obtained by Condensation of l-methyl-lpekhydrazine' with benzaldehyde and acetaldehyde. Since the very successful results obtained by cyclization of the arylglyoral hydrazones (1, with 75% sulfuric acid were probably due to the unique structure of the substrates involved (vide infra), it was not surprising that these a ) The abbreviation .poV stands for phenacyl ethylene ketal throughout this paper.


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Controlled Release of Volatile Aldehydes
✍ Barbara Levrand; Wolfgang Fieber; Jean-Marie Lehn; Andreas Herrmann 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 511 KB

## Abstract Delivery systems generated by reversible hydrazone formation from hydrazine derivatives (see __Fig. 1__) and carbonyl compounds in H~2~O efficiently increase the long‐lastingness of volatile aldehydes and ketones (R^1^R^2^CO) in various perfumery applications. The hydrazones are usuall