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DOI: 10.1039/A806025H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 3535-3540

ν-Triazolines. Part 40.1 Thermal and photochemical transformations of 1-biaryl-5-amino-4,5-dihydro-ν-triazoles: a new synthetic approach to 6-alkylphenanthridines and aza-analogs

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Emanuela Erba, Donato Pocar and Pasqualina Trimarco

Abstract

1-Biaryl-5-morpholino-ν-triazolines 4 were prepared from aliphatic aldehydes 1, morpholine and 2-azidobiaryls 3. They underwent smooth thermal rearrangement to tertiary amidines 5 which were photochemically cyclized to 6-alkylphenanthridines 6a,b,e,f and analogs 6c,d and 8a,b with morpholine elimination. Direct photolysis of triazolines 4 afforded lower yields of the same compounds 6 together with by-products indicative of the mechanism of the photochemical rearrangement which is discussed.

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