Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile : heterocyclic [3.3.3]propellanes

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Hassan , A A , Mohamed , N K , Aly , A A , Tawfeek , H N , Bräse , S & Nieger , M 2021 , ' Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile : heterocyclic [3.3.3]propellanes ' , Molecular Diversity , vol. 25 , no. 1 , pp. 99-108 . https://doi.org/10.1007/s11030-019-10027-8

Title: Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile : heterocyclic [3.3.3]propellanes
Author: Hassan, Alaa A.; Mohamed, Nasr K.; Aly, Ashraf A.; Tawfeek, Hendawy N.; Bräse, Stefan; Nieger, Martin
Contributor: University of Helsinki, Department of Chemistry
Date: 2021
Language: eng
Number of pages: 10
Belongs to series: Molecular Diversity
ISSN: 1381-1991
URI: http://hdl.handle.net/10138/327075
Abstract: Synthesis of heteropropellanes in one step: the reaction between dicyanomethylene-1,3-indanedione (CNIND) and N-substituted-2-(2,4-dinitrophenyl)hydrazinecarbothioamides, furnished (3aR,8bS,Z)-2-amino-9-substituted-10-(2-(2,4-dinitrophenyl)hydrazono)-4-oxo-4H-3a,8b-(epithiomethanoimino)indeno[1,2-b]furan-3-carbonitrile as a type of (2,4-dinitrophenyl)hydrazono[3.3.3]propellanes in good yields as single diastereomers. Structure determination and confirmation of the synthesized products have been achieved using various and modern spectroscopic techniques such as IR, NMR (H-1 NMR and(13)C NMR), mass spectrometry, as well as X-ray crystal analysis. The X-ray structure data cleared that the molecule of7awas crystalized as monoclinic, space group C2/c (no.15). [GRAPHICS] .
Subject: Annulated compounds
Heterocyclization
Imine-enamine tautomerism
Nucleophilic addition
Furothiazolo[3.3.3]propellanes
Thiosemicarbazides
REARRANGEMENT
SKELETON
CRYSTAL
AMINES
116 Chemical sciences
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