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The reaction of 5-alkoxyacridines with bases and their salts

✍ Scribed by Barber, H. J. ;Wilkinson, J. H. ;Edwards, V. G. H.

Publisher
Wiley (John Wiley & Sons)
Year
1947
Weight
621 KB
Volume
66
Category
Article
ISSN
0368-4075

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✦ Synopsis

Abstract

It has been shown that 5‐alkoxyacridines react with ammonium and primary amine salts under the relatively mild conditions employed for the conversion of imino‐ethers to amidines, ^1,2^ to give 5‐aminoacridines in good yield. Similar reactions occur with aminoacids but the salts of secondary bases do not react under these conditions. A number of examples are described and a probable reaction mechanism is suggested.

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The reaction of (OCH2CMe2CH20)P(O)CI (l)with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded the phosphonate salt [(OCH2CMe2CH20)P(O)(DBU)]+[CI] (3); the X ray structure of this compound as a hydrate shows that the C-6 (labeled as C I in Fig. 1) of the DBU is c:onnected to the phosphorus. In an an