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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Published in | Synthesis (Stuttgart) no. 5; pp. 503 - 508 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
1993
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Subjects | |
Online Access | Get more information |
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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. |
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ISSN: | 0039-7881 |
DOI: | 10.1055/s-1993-25893 |