Collect. Czech. Chem. Commun. 1983, 48, 1854-1863

1,3-Dipolar cycloadditions of C-benzoyl-N-phenylnitrone indole derivatives

Lubor Fišeraa, Peter Meskoa, Ján Leškob, Miloslava Dandárováa, Jaroslav Kováča and Igor Goljerc

a Department of Organic Chemistry
b Laboratory of Mass Spectrometry
c Laboratory of NMR Spectrometry, Slovak Institute of Technology, 880 37 Bratislava


Reaction of the title nitrone I with indole derivatives IIa,b gives the 1,3-addition product IIIa,b, its hydrogenated derivative IVa,b and dehydrogenation products VIa,b and VIIa,b from transient product of 1,3-dipolar cycloaddition (V). Indole itself only gives cycloaddition products VIc and VIIc. Carbazole derivative VIII does not react due to sterical reasons. The reaction course is discussed on the basis of PMO theory. Structure of the products has been proved by 1H and 13C NMR, IR, UV, and mass spectra.