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

✍ Scribed by László Somogyi; Attila Csaba Bényei

Book ID
102232933
Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
225 KB
Volume
20
Category
Article
ISSN
1042-7163

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✦ Synopsis

The tendency of acylhydrazones to undergo a spontaneous cyclization into 1,3,4oxadiazolines 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 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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✍ JoséG. Fernández-Bolaños; Salud García; José Fernández-Bolaños; María Jesús Dián 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 526 KB

2-Amino-2,3-dideoxy-D-glucitol-3-sulfonic acid (3) and 2-amino-2,6-dideoxy-o-glucitol-6sulfonic acid (4) were prepared by reduction of 2-amino-2,3 (and 2,6)-dideoxy-D-glucopyranose-3 (and 6)-sulfonic acids with sodium borohydride. The crystal structure of 4 monohydrate (C6H15NOTS.H20) is orthorhombi