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

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

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 m...

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Main Authors: Ashraf A. Aly, Nasr K. Mohamed, Alaa A. Hassan, Kamal M. El-Shaieb, Maysa M. Makhlouf, Stefan Bräse, Martin Nieger, Alan B. Brown
Format: Article
Language:English
Published: MDPI AG 2019-08-01
Series:Molecules
Subjects:
acenaphthequinone
4-acetyl[2.2]paracyclophane
thiosemicarbazone
dialkyl-acetylenedicarboxylates
1,3-thiazolidinones
DMAD tetramer
Online Access:https://www.mdpi.com/1420-3049/24/17/3069
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spelling doaj-8f481cb3f1464aaf889b7acce94a31d22020-11-25T00:57:30ZengMDPI AGMolecules1420-30492019-08-012417306910.3390/molecules24173069molecules24173069Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-ThiosemicarbazonesAshraf A. Aly0Nasr K. Mohamed1Alaa A. Hassan2Kamal M. El-Shaieb3Maysa M. Makhlouf4Stefan Bräse5Martin Nieger6Alan B. Brown7Chemistry Department, Faculty of Science, Minia University, El-Minia 61519, EgyptChemistry Department, Faculty of Science, Minia University, El-Minia 61519, EgyptChemistry Department, Faculty of Science, Minia University, El-Minia 61519, EgyptChemistry Department, Faculty of Science, Minia University, El-Minia 61519, EgyptChemistry Department, Faculty of Science, Minia University, El-Minia 61519, EgyptInstitute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, GermanyDepartment of Chemistry, University of Helsinki, P.O. Box 55, A. I. Virtasen aukio I, 00014 Helsinki, FinlandChemistry Program, Florida Institute of Technology, Melbourne, FL 32901, USAThe 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-(((<i>Z</i>,<i>E</i>)-<i>N</i>-allyl-<i>N</i>&#8242;-(2-oxoacenaphthylen-1(2<i>H</i>)-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 (<sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.https://www.mdpi.com/1420-3049/24/17/3069acenaphthequinone4-acetyl[2.2]paracyclophanethiosemicarbazonedialkyl-acetylenedicarboxylates1,3-thiazolidinonesDMAD tetramer
collection DOAJ
language English
format Article
sources DOAJ
author Ashraf A. Aly
Nasr K. Mohamed
Alaa A. Hassan
Kamal M. El-Shaieb
Maysa M. Makhlouf
Stefan Bräse
Martin Nieger
Alan B. Brown
spellingShingle Ashraf A. Aly
Nasr K. Mohamed
Alaa A. Hassan
Kamal M. El-Shaieb
Maysa M. Makhlouf
Stefan Bräse
Martin Nieger
Alan B. Brown
Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
Molecules
acenaphthequinone
4-acetyl[2.2]paracyclophane
thiosemicarbazone
dialkyl-acetylenedicarboxylates
1,3-thiazolidinones
DMAD tetramer
author_facet Ashraf A. Aly
Nasr K. Mohamed
Alaa A. Hassan
Kamal M. El-Shaieb
Maysa M. Makhlouf
Stefan Bräse
Martin Nieger
Alan B. Brown
author_sort Ashraf A. Aly
title Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
title_short Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
title_full Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
title_fullStr Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
title_full_unstemmed Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones
title_sort functionalized 1,3-thiazolidin-4-ones from 2-oxo-acenaphthoquinylidene- and [2.2]paracyclophanylidene-thiosemicarbazones
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-08-01
description 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-(((<i>Z</i>,<i>E</i>)-<i>N</i>-allyl-<i>N</i>&#8242;-(2-oxoacenaphthylen-1(2<i>H</i>)-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 (<sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.
topic acenaphthequinone
4-acetyl[2.2]paracyclophane
thiosemicarbazone
dialkyl-acetylenedicarboxylates
1,3-thiazolidinones
DMAD tetramer
url https://www.mdpi.com/1420-3049/24/17/3069
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