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Reactions of N- and C-Alkenylanilines: I. Synthesis of Anilides and Amidines from ortho-Alkenyl(cycloalkenyl)anilines and Their Transformations

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Abstract

N-Acetyl- and N-formyl-ortho-alkenyl(cycloalkenyl)anilines were synthesized. Their reaction with P2O5 or PCl5 afforded quinolines. By reaction of the ortho-alkenyl(cycloalkenyl)anilines with 1-methylimino- or 1-phenylimino-1-chloroethanes amidines were obtained that were cyclized in the polyphosphoric acid. The reaction with the polyphosphoric acid of amidines prepared from alkenylanilines and 1-methylimino-1-chloroethane gave rise to 3-methyl-3,4-dihydroquinazolines; on replacing in the substrate methylimine group for phenylimine one the yield of quinazoline decreased.

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Authors and Affiliations

  1. Ufa Scientific Center, Russian Academy of Sciencs, Ufa, Institute of Organic Chemistry, Bashkortostan, 450054, Russia

    R. R. Gataullin, I. S. Afon'kin, A. A. Fatykhov, L. V. Spirikhin & I. B. Abdrakhmanov

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  1. R. R. Gataullin
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  2. I. S. Afon'kin
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  3. A. A. Fatykhov
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  4. L. V. Spirikhin
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  5. I. B. Abdrakhmanov
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Gataullin, R.R., Afon'kin, I.S., Fatykhov, A.A. et al. Reactions of N- and C-Alkenylanilines: I. Synthesis of Anilides and Amidines from ortho-Alkenyl(cycloalkenyl)anilines and Their Transformations. Russian Journal of Organic Chemistry 37, 834–840 (2001). https://doi.org/10.1023/A:1012413715466

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