THE PREPARATION OF N-(1H-PYRAZOL-3-YL)ARYLAMIDES AND 1H-PYRAZOL-3-AMINES FROM POLYLITHIATED C(ALPHA),N-THIOSEMICARBAZONES AND C(ALPHA),N-SEMICARBAZONES
Cf. Beam et al., THE PREPARATION OF N-(1H-PYRAZOL-3-YL)ARYLAMIDES AND 1H-PYRAZOL-3-AMINES FROM POLYLITHIATED C(ALPHA),N-THIOSEMICARBAZONES AND C(ALPHA),N-SEMICARBAZONES, Journal of heterocyclic chemistry, 34(5), 1997, pp. 1549-1554
C(alpha),N-Thiosemicarbazones or C(alpha),N-semicarbazones were polyli
thiated with excess lithium diisopropylamide, and the resulting cycliz
ed intermediates were condensed with aromatic esters to afford N-(1H-p
yrazol-3-yl)arylamides. The polylithiated intermediates were also quen
ched with aqueous acid to give 5-substituted, 1H-pyrazol-3-amines.