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Synthesis 1993; 1993(5): 503-508
DOI: 10.1055/s-1993-25893
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Efficient Synthesis of a Range of Benzo-Substituted Macrocyclic Diamides

Yehia A. Ibrahim* , Ahmed H. M. Elwahy
  • *Department of Chemistry, Faculty of Science, Cairo University, Giza, A. R. Egypt
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Publication Date:
17 September 2002 (online)

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Sixteen new 14-17-macrocyclic dibenzo and tribenzodioxadiamides and trioxadiamides (macrooxacyclams, e.g., 5,6,7,8,9,10,16,17-octahydrodibenzo [e,m][1,4,8,11 ]dioxadiazatetradecine-5,10-dione) 13-28 have been prepared. Moderate to good yields (40-90%) of 13-28 were achieved in the macrocyclization step by reacting the dipotassium salts of 1,2-bis(2-hydroxybenzoylamino)ethanes 6, 7 and 1,2-bis (2-hydroxybenzoylamino)benzenes 8, 9 with the appropriate dihaloalkane or ditosylate in dimethylformamide. Alkylation of 13 and 25 with an appropriate halo compound in tetrahydrofuran and sodium hydride yielded the corresponding N,N-dialkylmacro-oxacyclams 29-33. The stereochemical purity of the latter was proved by 1H NMR and 13C NMR.