Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones

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Aly , A A , Mohamed , N K , Hassan , A A , El-Shaieb , K M , Makhlouf , M M , Bräse , S , Nieger , M & Brown , A B 2019 , ' Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones ' , Molecules , vol. 24 , no. 17 , 3069 . https://doi.org/10.3390/molecules24173069

Title: Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
Author: Aly, Ashraf A.; Mohamed, Nasr K.; Hassan, Alaa A.; El-Shaieb, Kamal M.; Makhlouf, Maysa M.; Bräse, Stefan; Nieger, Martin; Brown, Alan B.
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-09-01
Language: eng
Number of pages: 20
Belongs to series: Molecules
ISSN: 1420-3049
URI: http://hdl.handle.net/10138/306491
Abstract: The reactions of dialkyl acetylenedicarboxylates with various 2-oxo-acenaphthoquinylidene- and 4-acetyl[2.2]paracyclophanylidene-thiosemicarbazones were investigated. Using simple experimental procedures, 1,3-Thiazolidin-4-ones derived from acenaphthequinone or [2.2]paracyclophane were obtained as major products in good yields. In the case of allyl derivative of acenaphthoquinylidene-thiosemicarbazones, a complex structure of tetramethyl 5-(2-(((Z,E)-N-allyl-N'-(2-oxoacenaphthylen-1(2H)-ylidene)carbamohydrazonoyl)thio)-1,2,3-tris-(methoxycarbonyl)-cyclopropyl)-4-methoxy-7-oxabicyclo[2.2.1]hepta-2,5-diene-1,2,3,6-tetracarboxylate was formed. Single crystal X-ray analysis was used as an efficient tool to confirm the structure of the synthesized compounds as well as different spectroscopic data (H-1-NMR, C-13-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.
Subject: acenaphthequinone
4-acetyl[2.2]paracyclophane
thiosemicarbazone
dialkyl-acetylenedicarboxylates
1,3-thiazolidinones
DMAD tetramer
1,3-DIPOLAR CYCLOADDITION
EFFICIENT SYNTHESIS
DIMETHYL ACETYLENEDICARBOXYLATE
ANTIOXIDANT
THIOSEMICARBAZONES
HETEROCYCLES
DERIVATIVES
HYDRAZINECARBOTHIOAMIDE
THIAZOLIDIN-4-ONES
3-COMPONENT
116 Chemical sciences
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