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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][1,7]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 HCl slowly transformed to give compound 5 as a major product. |
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