Abstract <p>A method for the synthesis of pyrazolo[3,4-<i>f</i>]quinolines from 6-aminoindazole and 4<i>H</i>-chromene-3-carbaldehydes or their fused analogs has been developed. It has been established that the reaction of β-trifluoroacetyl-substituted 4<i>H</i>-chromenes with 6-aminoindazole proceeds regioselectively to afford 9-trifluoromethylpyrazolo[3,4-<i>f</i>]quinolines. It has also been demonstrated that in reactions with 4<i>H</i>-chromene-3-carbaldehydes or 1<i>H</i>-benzo[<i>f</i>]chromene-2-carbaldehydes, 3-aminoindazoles act as 1,3-<i>N</i>,<i>N</i>-binucleophiles, thereby providing access to pyrimido[1,2-<i>b</i>]indazoles.</p>

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[3+3]-Cyclocondensation of β-Carbonyl-Substituted 4H-Chromenes with 3- and 6-Aminoindazoles: Synthesis of Pyrimido[1,2-b]indazoles and Pyrazolo[3,4-f]quinolines

  • Dmitry V. Osipov,
  • Pavel E. Krasnikov,
  • Oleg P. Demidov,
  • Vitaly A. Osyanin

摘要

Abstract

A method for the synthesis of pyrazolo[3,4-f]quinolines from 6-aminoindazole and 4H-chromene-3-carbaldehydes or their fused analogs has been developed. It has been established that the reaction of β-trifluoroacetyl-substituted 4H-chromenes with 6-aminoindazole proceeds regioselectively to afford 9-trifluoromethylpyrazolo[3,4-f]quinolines. It has also been demonstrated that in reactions with 4H-chromene-3-carbaldehydes or 1H-benzo[f]chromene-2-carbaldehydes, 3-aminoindazoles act as 1,3-N,N-binucleophiles, thereby providing access to pyrimido[1,2-b]indazoles.