Contributions to the chemistry of 3‐cyanoacetylhydrazono‐2‐indolinones and X‐ray structure of  Z ‐3‐cyanoacetylhydrazono‐2‐indolinone monohydrate | Zendy

Somogyi László | Zendy; Bényei Attila Csaba | Zendy

Open Access

Contributions to the chemistry of 3‐cyanoacetylhydrazono‐2‐indolinones and X‐ray structure of Z ‐3‐cyanoacetylhydrazono‐2‐indolinone monohydrate

Author(s) -

Somogyi László,

Bényei Attila Csaba

Publication year - 2009

Publication title -

heteroatom chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.283

H-Index - 42

eISSN - 1098-1071

pISSN - 1042-7163

DOI - 10.1002/hc.20531

Subject(s) - chemistry , heteroatom , intramolecular force , hydrazone , hydrogen bond , crystal structure , stereochemistry , medicinal chemistry , crystallography , molecule , organic chemistry , alkyl

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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