Structural Studies on Bioactive Compounds. Part 31. Interaction of 9-azidoacridine and 1-morpholinocyclohexene: Formation,Decomposition and Rearrangement of the Intermediate 1,2,3-triazoline †
Free accessOtherFirst published online February, 2000
Structural Studies on Bioactive Compounds. Part 31. Interaction of 9-azidoacridine and 1-morpholinocyclohexene: Formation,Decomposition and Rearrangement of the Intermediate 1,2,3-triazoline †
9-Azidoacridine 1 and the cyclic enamine 2 undergo a selective 1,3-dipolar cycloaddition reaction to give the 1,2,3-triazoline 3 with the expected regiochemistry. Exposure of the triazoline 3 to methanol induces the extrusion of nitrogen accompanied by a ring contraction to furnish the amidino-acridine 5 in high yield.
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