Contributions to the chemistry of 3-cyanoacetylhydrazono-2-indolinones and x-ray structure of z-3-cyanoacetylhydrazono-2-indolinone monohydrate

László Somogyi, A. Bényei

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 1-methyl-and 1-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 N-H and oxygen atom of the indolinone carbonyl, and in this way the Z isomer over the C=N bond is stabilized.

Original languageEnglish
Pages (from-to)183-193
Number of pages11
JournalHeteroatom Chemistry
Volume20
Issue number4
DOIs
Publication statusPublished - 2009

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Isomers
X rays
Isatin
Hydrazones
Acetylation
Stereoisomerism
Cyclization
Hydrogen bonds
Crystal structure
Oxygen
Derivatives
Atoms
2-oxindole
1-acetylisatin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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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 1-methyl-and 1-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 N-H and oxygen atom of the indolinone carbonyl, and in this way the Z isomer over the C=N bond is stabilized.",
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T1 - Contributions to the chemistry of 3-cyanoacetylhydrazono-2-indolinones and x-ray structure of z-3-cyanoacetylhydrazono-2-indolinone monohydrate

AU - Somogyi, László

AU - Bényei, A.

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N2 - 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 1-methyl-and 1-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 N-H and oxygen atom of the indolinone carbonyl, and in this way the Z isomer over the C=N bond is stabilized.

AB - 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 1-methyl-and 1-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 N-H and oxygen atom of the indolinone carbonyl, and in this way the Z isomer over the C=N bond is stabilized.

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