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Reaction of 3-amino-acridine with formaldehyde in acidic medium: Influence of the stoechiometry on the reaction products

✍ Scribed by Arnaud Tatibouët; Noémie Fixler; Martine Demeunynck; Jean Lhomme

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
471 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

3-amino-acridine 1 reacts with formaldehyde in acidic medium to give four different compounds depending on the stoechiometry of the reaction: the dihydrooxazine derivative 2, the tetrahydropyrimidine derivative 3, the TrOger's Base analogue 4 and the acridino[3,4-j]benzo[b][l,7]phenanthroline 5. Compounds 3, 4 and 5 could be obtained selectively by using the required amount of formaldehyde. Selective synthesis of 2 was independently realized in a three step sequence. Compounds 2, 3 and 4 in solution in 12 N HCI slowly transformed to give compound 5 as a major product.

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