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Synthesis of chromophoric bisazocrowndilactams

✍ Scribed by Yehia A. Ibrahim; Ahmed H. M. Elwahy; Gamal M. M. El-Kareish

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 319 KB
Volume: 6
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520060213

No coin nor oath required. For personal study only.

✦ Synopsis

The coupling of 1,2-bis(o-hydroxybenzamido)ethane

1 with two equivalents of the appropriate arenediazonium chloride in aqueous sodium hydroxide afforded the corresponding I ,2-bis(2-hydroxy-5-aryl-azobenzoy1amino)ethanes 4-6. The latter were converted to the corresponding dipotassium salts 7-9, which were reacted with the appropriate dihalo compound or ditosylate in boiling DMF to give the corresponding 14-1 7-membered macrocyclic bis-azoc r d i l a c t a m s 10-18 in 5845% yields. Compound 14 was N-alkylated to give the corresponding N,N'dibenzyl derivative 19.

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