Contributions to the chemistry of 3-cyanoacetylhydrazono-2-indolinones and X-ray structure of Z-3-cyanoacetylhydrazono-2-indolinone monohydrate
Corresponding Author
László Somogyi
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, HungarySearch for more papers by this authorAttila Csaba Bényei
Department of Physical Chemistry, Laboratory for X-ray Diffraction, University of Debrecen, P.O. Box 7, H-4010 Debrecen
Search for more papers by this authorCorresponding Author
László Somogyi
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, HungarySearch for more papers by this authorAttila Csaba Bényei
Department of Physical Chemistry, Laboratory for X-ray Diffraction, University of Debrecen, P.O. Box 7, H-4010 Debrecen
Search for more papers by this authorAbstract
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 (www.interscience.wiley.com). DOI 10.1002/hc.20531
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