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The C,N double bond of pyridine, quinoline and isoquinoline as heterodipolarophile react with diarylnitrilimines 2, generated in situ by dehydrohalogenation of N-phenylbenzhydrazonoyl chlorides 1, in a cycloaddition with complete regioselectivity.A facile route to hitherto unreported 1,3-diaryl-1,8a-dihydro<1,2,4>triazolo<4,3-a>pyridines 3, 1,3-diaryl-3,3a-dihydro<1,2,4>triazolo<4,3-a>quinolines 4, and 1,3-diaryl-1,10b-dihydro<1,2,4>triazolo<3,4-a>isoquinolines 5 has been developed.In a similar way, cycloadditions are carried out with C-ethoxycarbonyl- and C-acetyl-N-phenylnitrilimines.The ring cleavage of 3 in acidic medium yields the corresponding <(arylhydrazono)methyl>pyridinium chlorides 7.The conversion of the open-chain products back to 3 has been carried out in pyridine containing triethylamine.Anodic oxidation of 3 – 5 in aprotic medium affords the <1,2,4>triazolohetarenium perchlorates 9 – 11.The yields in such reactions are either similar or better than with chemical oxidants.The thermally initiated cycloreversion of 3 and 5 is discussed, judging from the facts that the thermolysis afford 2:1 cycloadducts.Key Words: Nitrilimines / <1,2,4>Triazolopyridines / 1,3-Dipolar cycloadditions
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Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis