Conclusions
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1.
Nonsterically hindered primary arylamines react with hexafluoroacetone benzenesulfonyl- and trifluoroacetylimines to give stable gem-diamino compounds.
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2.
The presence of substituents at the nitrogen of the arylamine destabilizes these gem-diamino compounds, with the formation of C2- and C4-alkylation products. With hexafluoroacetone trifluoroacetylimine, C2-alkylation is accompanied by heterocyclization to give 1-substituted 2,4,4-tris(trifluoroacetyl)-1,4-dihydroquinazolines.
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3.
N,N-Dialkylanilines are regioselectively alkylated at C4.
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 126–132, January, 1989.
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Chkanikov, N.D., Vershinin, V.L., Galakhov, M.V. et al. Reactions of hexafluoroacetone benzenesulfonyl- and trifluoroacetylimines with arylamines. Russ Chem Bull 38, 113–119 (1989). https://doi.org/10.1007/BF00953713
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DOI: https://doi.org/10.1007/BF00953713