Reactive intermediates in the reaction of hydrazinecarbothioamides with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate

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Aly , A A , Hassan , A A , Mohamed , N K , El-Shaieb , K M , Makhlouf , M M , Bräse , S & Nieger , M 2019 , ' Reactive intermediates in the reaction of hydrazinecarbothioamides with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate ' , Research on Chemical Intermediates , vol. 45 , no. 2 , pp. 613-631 . https://doi.org/10.1007/s11164-018-3633-4

Title: Reactive intermediates in the reaction of hydrazinecarbothioamides with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate
Author: Aly, Ashraf A.; Hassan, Alaa A.; Mohamed, Nasr K.; El-Shaieb, Kamal M.; Makhlouf, Maysa M.; Bräse, Stefan; Nieger, Martin
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-02
Language: eng
Number of pages: 19
Belongs to series: Research on Chemical Intermediates
ISSN: 0922-6168
URI: http://hdl.handle.net/10138/310813
Abstract: The reaction of N-substituted hydrazinecarbothioamides with both 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate afforded various heterocyclic rings such as 5-amino-4-cyano-3-(methylthio)-N-phenyl-1H-pyrazole-1-carbothioamide, 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, 4-substituted-3-(substituted amino)-1H-1,2,4-triazole-5(4H)-thione, ethyl 5-amino-3-(methylthio)-1-(substituted carbamothioyl)-1H-pyrazole-4-carboxylate, and (Z)-ethyl 2-cyano-2-(5-(substituted amino)-1,3,4-thiadiazol-2(3H)-ylidene)acetate. However, under gentle heating, the reaction of the same starting substances behaved differently. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses as well as single-crystal X-ray diffraction analysis. [GRAPHICS] .
Subject: N-substituted hydrazinecarbothioamides
2-(Bis(methylthio)methylene)malononitriles
Reactive intermediates
Various heterocycles
X-ray structure analyses
PYRAZOLE DERIVATIVES
ANTIDEPRESSANT
116 Chemical sciences
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