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The manuscript describes the synthesis of new racemic and chiral linked paracyclophane assigned as N -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 target Sp - Sp - N -5-(1,4(1,4)-dibenzenacyclohexaphane-1 2 -yl)carbamoyl)-5'-(1,4(1,4)-dibenzenacyclohexaphane-1 2 -yl)carboxamide. Subjecting N -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-3 H -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.

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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