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A rapid analogue synthesis of biologically active 3,6,7-trisubstituted 1,2,4-triazolo[4,3-b]pyridazines was devised to give easy and selective variation of the three substituents through combinations of silicon-directed anion formation, palladium-catalysed couplings and S N Ar displacements.
A rapid and convenient synthesis of the 3-trifluoromethanesulfonyloxy-2-pyridone 2, one of the first examples of this class of compound, was achieved by Vilsmeier formylation and cyclisation of the acyl enamine 6. The triflate 2 was found to undergo a range of palladium-catalysed coupling reactions giving a synthetic sequence of general use for the preparation of highly substituted 2-pyridones.
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