Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds

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Hassan , A A , Aly , A A , Mohamed , N K , El-Shaieb , K M , Makhlouf , M M , Bräse , S , Nieger , M & Brown , A B 2020 , ' Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds ' , Research on Chemical Intermediates , vol. 46 , no. 2 , pp. 1571–1585 . https://doi.org/10.1007/s11164-019-04051-4

Title: Reactivity of N-substituted alkenylidene hydrazinecarbothioamides toward tetracyanoethylene, an efficient synthesis stereoselective 1,3-thiazole compounds
Author: Hassan, Alaa A.; Aly, Ashraf A.; Mohamed, Nasr K.; El-Shaieb, Kamal M.; Makhlouf, Maysa M.; Bräse, Stefan; Nieger, Martin; Brown, Alan B.
Contributor organization: Department of Chemistry
Date: 2020-02
Language: eng
Number of pages: 15
Belongs to series: Research on Chemical Intermediates
ISSN: 0922-6168
DOI: https://doi.org/10.1007/s11164-019-04051-4
URI: http://hdl.handle.net/10138/322255
Abstract: The reaction between N-substituted alkenylidene hydrazinecarbothioamides and two molar amounts of tetracyanoethylene (TCNE) in anhydrous THF at room temperature without using any catalyst affords (Z)-4-amino-3-((Z)substituted amino)-2-(substituted imino)-2,3-dihydrothiazole-5-carbonitriles and (Z)-(4-amino-5-cyano-thiazol-2(3H)-ylidene)carbonhydrazonoyl dicyanides. Rationales for these transformations are presented. The structures of the obtained products were confirmed via single-crystal X-ray analyses. Graphic Here, we synthesize (Z)-4-amino-3-amino-2-imino-2,3-dihydrothiazole-5-carbonitriles and (Z)-(4-amino-5-cyano-thiazol-2(3H)-ylidene)carbonhydrazonoyl dicyanides from the reaction of N-substituted alkenylidene hydrazinecarbothioamides with (TCNE) in anhydrous THF at room temperature without using any catalyst. [GRAPHICS] .
Subject: N-Substituted alkenylidene hydrazinecarbothioamides
Tetracyanoethylene
Stereoselective 1
3-thiazole derivatives
Donor-acceptor interaction
X-ray crystallography
DERIVATIVES
THIAZOLE
CHEMISTRY
DESIGN
116 Chemical sciences
Peer reviewed: Yes
Rights: unspecified
Usage restriction: openAccess
Self-archived version: acceptedVersion


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