Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles

Show full item record



Permalink

http://hdl.handle.net/10138/319602

Citation

Aly , A A , Bräse , S , Hassan , A A , Mohamed , N K , Abd El-Haleem , L E & Nieger , M 2020 , ' Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles ' , Molecules , vol. 25 , no. 15 , 3315 . https://doi.org/10.3390/molecules25153315

Title: Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles
Author: Aly, Ashraf A.; Bräse, Stefan; Hassan, Alaa A.; Mohamed, Nasr K.; Abd El-Haleem, Lamiaa E.; Nieger, Martin
Contributor: University of Helsinki, Department of Chemistry
Date: 2020-08
Language: eng
Number of pages: 19
Belongs to series: Molecules
ISSN: 1420-3049
URI: http://hdl.handle.net/10138/319602
Abstract: The manuscript describes the synthesis of new racemic and chiral linked paracyclophane assigned asN-5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)carbamoyl)-5'-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)carboxamide. The procedure depends upon the reaction of 5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)hydrazide with 5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)isocyanate. To prepare the homochiral linked paracyclophane of a compound, the enantioselectivity of 5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)carbaldehyde (enantiomeric purity 60% ee), was oxidized to the corresponding acid, which on chlorination, gave the corresponding acid chloride of [2.2]paracyclophane. Following up on the same procedure applied for the preparation of racemic-carbamoyl and purified by HPLC purification, we succeeded to obtain the targetSp-Sp-N-5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)carbamoyl)-5'-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)carboxamide. SubjectingN-5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)hydrazide to various isothiocyanates, the corresponding paracyclophanyl-acylthiosemicarbazides were obtained. The latter compounds were then cyclized to a new series of 5-(1,4(1,4)-dibenzenacyclohexaphane-1(2)-yl)-2,4-dihydro-3H-1,2,4-triazol-3-thiones. 5-(1,4(1,4)-Dibenzenacyclohexaphane-1(2)-yl)-1,3,4-oxadiazol-2-amines were also synthesized in good yields via internal cyclization of the same paracyclophanyl-acylthiosemicarbazides. NMR, IR, and mass spectra (HRMS) were used to elucidate the structure of the obtained products. The X-ray structure analysis was also used as an unambiguous tool to elucidate the structure of the products.
Subject: HPLC
chiralN-([2
2]-paracyclophanylcarbamoyl)-4-([2
2] paracyclophanylcarboxamide
hydrazinecarbothioamide-paracyclophanes
paracyclophanyl-1
2
4-triazol-3-thione
paracyclophanyl)-1
3
4-oxadiazoles
BIOLOGICAL EVALUATION
1,3,4-OXADIAZOLE DERIVATIVES
HYDRAZONE DERIVATIVES
ONE-POT
INHIBITORS
COMPLEX
ANTIBACTERIAL
HETEROCYCLES
DISCOVERY
DESIGN
116 Chemical sciences
Rights:


Files in this item

Total number of downloads: Loading...

Files Size Format View
molecules_25_03315.pdf.part 7.876Mb Unknown View/Open

This item appears in the following Collection(s)

Show full item record