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- Title
Contributions to the chemistry of 3-cyanoacetylhydrazono-2-indolinones and X-ray structure of Z-3-cyanoacetylhydrazono-2-indolinone monohydrate.
- Authors
Somogyi, László; Bényei, Attila Csaba
- Abstract
The tendency of acylhydrazones to undergo a spontaneous cyclization into 1,3,4-oxadiazolines has been investigated. Contrary to the literature data, an attempted transformation of isatin cyanoacetylhydrazone in solution generates stereoisomers and not the reported structural isomer oxadiazoline. A similar behavior of the corresponding l-methyl- and l-acetylisatin derivatives even under acetylation conditions has been found. The crystal structure of the Z isomer of 3-cyanoacetylhydrazono-2-indolinone monohydrate is reported. It contains strong intramolecular hydrogen bond between the hydrazone NH and oxygen atom of the indolinone carbonyl, and in this way the Z isomer over the CN bond is stabilized. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:183-193, 2009; Published online in Wiley InterScience (). DOI 10.1002/hc.20531
- Publication
Heteroatom Chemistry, 2009, Vol 20, Issue 4, p183
- ISSN
1042-7163
- Publication type
Article
- DOI
10.1002/hc.20531