Regioselective synthesis of 5-aminopyrazoles from reactions of amidrazones with activated nitriles : NMR investigation and X-ray structural analysis

Show full item record



Permalink

http://hdl.handle.net/10138/309262

Citation

Aly , A A , Ramadan , M , Al-Aziz , M A , Bräse , S , Brown , A B , Fathy , H M & Nieger , M 2017 , ' Regioselective synthesis of 5-aminopyrazoles from reactions of amidrazones with activated nitriles : NMR investigation and X-ray structural analysis ' , Chemical Papers , vol. 71 , no. 8 , pp. 1409-1417 . https://doi.org/10.1007/s11696-017-0131-x

Title: Regioselective synthesis of 5-aminopyrazoles from reactions of amidrazones with activated nitriles : NMR investigation and X-ray structural analysis
Author: Aly, Ashraf A.; Ramadan, Mohamed; Al-Aziz, Mohamed Abd; Bräse, Stefan; Brown, Alan B.; Fathy, Hazem M.; Nieger, Martin
Contributor organization: Department of Chemistry
Date: 2017
Language: eng
Number of pages: 9
Belongs to series: Chemical Papers
ISSN: 0366-6352
DOI: https://doi.org/10.1007/s11696-017-0131-x
URI: http://hdl.handle.net/10138/309262
Abstract: N-Arylbenzamidrazones and ethyl 2-cyano-3-ethoxybut-2-enoate reacted together in ethanol and catalyzed by triethylamine (Et3N) to give 5-amino-3-methyl-1-(aryl(phenylimino)methyl)-1H-pyrazole derivatives. Reaction of the target amidrazones with bis-(methylthio)methylidene)malononitrile in EtOH/Et3N/DMF mixture proceeded to give the corresponding 5-aminopyrazoles. The structure of the obtained products was proved by IR, mass, and NMR spectra and elemental analyses. Two-dimensional NMR spectroscopy and X-ray structural analyses were used to differentiate the assigned structures from other possible ring systems and regioisomers. The reaction mechanism is discussed.
Subject: 116 Chemical sciences
Peer reviewed: Yes
Rights: unspecified
Usage restriction: openAccess
Self-archived version: acceptedVersion


Files in this item

Total number of downloads: Loading...

Files Size Format View
Chemical_Papers ... st_revised_Hazem_paper.pdf 862.7Kb PDF View/Open

This item appears in the following Collection(s)

Show full item record