140-87-4

BROWN GRANULAR CRYSTALLINE POWDER

2-Cyanoacetohydrazide is used in the study of the viral inhibiting activity of some potential antiviral agents.

Cyanoacetic acid hydrazide was obtained by careful addition of hydrazine hydrate to ethyl cyanoacetate in ethanol with stirring at 0°C.[1]

Cyanoacetic acid hydrazide is a versatile and convenient intermediate for the synthesis of wide variety of heterocyclic compounds. The β-functional nitrile1-4 moiety of the molecule is a favorable unit for addition followed by cyclization or via cycloaddition with numerous reagents providing heterocyclic compounds of different ring sizes with one or several heteroatoms that are interesting as pharmaceuticals, as herbicides, as antibacterial agents, and as dyes. Their reactions with dinucleophiles usually result in the formation of polycyclic ring systems which may be the skeleton of important heterocylic compounds. In previous publications, novel synthesis of azoles, azines, and azoloazines, had been reported utilizing β-functional nitriles as starting components. Among the β-functional nitriles, cyanoacetic acid hydrazide and their analogues are especially important starting materials or intermediates for the synthesis of various nitrogen-containing heterocyclic compounds. Our research deals with the effective use of cyanoacetic acid hydrazide in the synthesis of a variety of polyfunctional heterocyclic compounds with biological interest.

Cyanoacetic acid hydrazide can act as an ambident nucleophile, that is, as both an N- and a C nucleophile. On treatment of cyanoacetic acid hydrazide with various reagents, the attack can take place at five possible sites: the nucleophile is able to attack the carbon of the carbonyl function (position 3) and the carbon atom of the nitrile function (position 5). While the active methylene group (position 4) and amino groups (positions 1 and 2) are able to attack electrophiles.

Crystallise the hydrazide from EtOH. The hydrochloride has m 178-180o and the benzylidene derivative has m 178o. It is converted to 3-oxo-5-iminopyrazolidine in hot 40% aqueous NaOH. [Beilstein 2 H 591, 2 I 256, 2 III 1636.] IRRITANT.

[1] Gorobets, N. Yu., Yousefi, B. H., Belaj, F., & Kappe, C. O. (2004). Rapid Microwave-Assisted Solution Phase Synthesis of Substituted 2-Pyridone Libraries. ChemInform, 36 2. https://doi.org/10.1002/chin.200502139 
[2] Elnagdi, M. H., Elmoghayar, M. R. H., & Elgemeie, G. E. H. (1984). The chemistry of 3-oxoalkanenitriles. Synthesis, 1984(01), 1-26. 
[3] Gaber, A. E.-A. M., El-Gaby, M. S. A., El-Dean, A. M. K., Eyada, H. A., & Al-Kamali, A. S. N. (2013). Synthesis of Novel Polyfunctionally Substituted Thieno[2,3-c]pyridazines. 51 6, 1325–1331. https://doi.org/10.1002/jccs.200400192
[4] Elagamey, A. G. A., El-Taweel, F. M. A. A., Khodeir, M. N. M., & Elnagdi, M. H. (1993). Nitriles in Heterocyclic Synthesis. The Reaction of Polyhydric Naphthalenes, 4-Methylcoumarin-3-carbonitrile, and Alkylidenemalononitrile with Methylenemalononitrile. Bulletin of the Chemical Society of Japan, 66(2), 464-468.