Synthesis of 1, 1-Disubstituted-3-aminoguanidines (Part 2)

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  • TOKU Hiroshige
    Department of Chemistry, School of Hygienic Sciences, Kitasato University
  • SATO Tadashi
    Department of Chemistry, School of Hygienic Sciences, Kitasato University
  • NISHIMURA Tamio
    Department of Chemistry, School of Hygienic Sciences, Kitasato University

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  • 1, 1-ジ置換-3-アミノグアニジンの合成 (第2報)
  • 1 , 1-ジ チカン 3 アミノグアニジン ノ ゴウセイ 2

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The reaction of acetone S-alkylisothiosemicarbazone (1) with pyrrolidine, piperidine and morpholine gave the corresponding new acetone [1, 1-disubstituted amidino] hydrazones (2). The reactivity of amines toward (1) decreased in the order of morpholine, pyrrolidine and piperidine. The reactvity of acetone S-methylisothiosemicarbazone toward amines was higher than that of acetone S-ethylisothiosemicarbazone. This reaction was inferred to proceed by an addition-elimination mechanism in which the amine adds to (1), and then the mercaptane is eliminated from the addition product, since acetylideneaminocyanamide failed to react with the amines.<BR>1, 1-Disubstituted-3-aminoguanidines were obtained by hydrolysis of (2) in good yields. The reaction of m-nitrobenzaldehyde with (2) in acidic ethanol gave quantitatively the corresponding 1, 1-disubstituted amidinohydrazones of m-nitrobenzaldehyde.

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