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Effective synthesis of new benzo-fused macrocyclic and heteromacrocyclic bis(Schiff bases)

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Abstract

In this study, the synthons 2-hydroxy-5-((arylthio)methyl)benzaldehydes were reacted with 1,ω-dihaloalkanes to produce the corresponding bis(aldehydes). The previous precursors were reacted with the appropriate alkane-1,ω-diamines in glacial acetic acid to yield a new series of macrocyclic bis(Schiff bases). Following that, a new series of thiamacrocyclic bis(Schiff bases) were synthesized in glacial acetic acid via sodium acetate-mediated cyclocondensation of the appropriate of 2,2'-(alkane-1,ω-diylbis(sulfanediyl))dianiline dihydrochloride with bis(aldehydes). Moreover, bis(4-amino-4H-1,2,4-triazole-3-thiol), linked to propane core via thioether, was cyclocondensed with bis(aldehydes) in glacial acetic acid to prepare new S-triazole-fused thiamacrocyclic bis(Schiff bases). The previous macrocycles were reacted with two equivalents of iodomethane in methanolic sodium methoxide solution to give macrocyclic bis(methylthio) derivatives. Surprisingly, the reaction of thieno[2,3-b]thiophene-linked bis(4-amino-3-phenyl-4H-1,2,4-triazole) with the appropriate bis(aldehydes) in glacial acetic acid resulted in a new series [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-fused macrocycles. All of the new macrocycles were synthesized with good to excellent yields, and their structures were deduced using elemental and spectral data.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt

    Ahmed A. M. Ahmed, Ahmed E. M. Mekky & Sherif M. H. Sanad

  2. Common First Year Deanship, Jouf University, Sakaka, Saudi Arabia

    Ahmed A. M. Ahmed

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Ahmed, A.A.M., Mekky, A.E.M. & Sanad, S.M.H. Effective synthesis of new benzo-fused macrocyclic and heteromacrocyclic bis(Schiff bases). J IRAN CHEM SOC 19, 1711–1722 (2022). https://doi.org/10.1007/s13738-021-02409-3

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