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.
References
1.
Part 30. CodyV., ChanD., GalitskyN., RakD., LuftJ. R., PangbornW., QueenerS. F., LaughtonC. A., and StevensM. F. G.Biochemistry, in press.
2.
HaganD.J., Giménez-ArnauE., SchwalbeC. H., and StevensM. F. G., J. Chem. Soc., Perkin Trans. 1, 1997, 2739–2746.
3.
JulinoM., and StevensM. F. G., J. Chem. Soc., Perkin Trans. 1, 1998, 1677–1684.
4.
KadabaP.K., StanovnikB., and TislerM., Adv. Heterocycl. Chem., 1984, 37, 217.
5.
PalaciosF., Ochoa de RetanaA. M., and PagaldayJ., Heterocycles, 1995, 40, 543.
6.
ErbaE., MaiG., and PocarD., J. Chem. Soc., Perkin Trans. 1, 1992, 2709.
7.
BecalliE.M., ErbaE., GelmiM. L., and PocarD., J. Chem. Soc., Perkin Trans. 1, 1996, 1359.
8.
Semiempirical calculations were done using MOPAC 7.0 implemented on a Silicon Graphics 10000 Extreme workstation. The PM3 parameters were chosen to calculate the optimised geometry (BFGS procedure). Energy minimisation was done in the PRECISE option. Stationary points were characterised as minima on the energy surface using the FORCE keyword. For PM3 see: StewartJ. J. P.Comput. Chem., 1989, 10, 209 and 221; J.J.P. Stewart, J. Comput. Chem., 1991, 12, 320;. J.J.P. Stewart, J. Comp.-Aided Mol. Design, 1990, 4, 1.
9.
SheldrickG. M., SHELX86, Program for Crystal Structure Solution, Acta Crystallogr., Sect. A, 1990, 46, 467.
10.
SheldrickG. M., SHELX93, University of Göttingen, Germany, 1993.
11.
WatkinD. J., ProutC. K., and PearceL. J., CAMERON, Chemical Crystallography Laboratory, University of Oxford, 1996.
