EFFICIENT SYNTHESIS OF A RANGE OF BENZO-SUBSTITUTED MACROCYCLIC DIAMIDES

Sixteen new 14-17-macrocyclic dibenzo and tribenzodioxadiamides and trioxadiamides (macrooxacyclams, e. g., 5,6,7,8,9,10,16,17-oc-tahydrodibenzo[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 s...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 5; pp. 503 - 508
Main Authors IBRAHIM, YA, ELWAHY, AHM
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXYGEN
CROWN COMPOUNDS
RECOGNITION
LIGANDS
COPPER(II)
COBALT(II)
ZINC(II)
RECEPTORS
SELECTIVITY
NICKEL(II)
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Summary:Sixteen new 14-17-macrocyclic dibenzo and tribenzodioxadiamides and trioxadiamides (macrooxacyclams, e. g., 5,6,7,8,9,10,16,17-oc-tahydrodibenzo[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 H-1 NMR and C-13 NMR.
ISSN:0039-7881
DOI:10.1055/s-1993-25893