G. Verardo et al., 1-SUBSTITUTED 1,4,5,6-TETRAHYDROPYRIDAZINES AND 1-(N-SUBSTITUTED)AMINOPYRROLIDINES FROM HYDRAZINES AND 2,5-DIMETHOXYTETRAHYDROFURAN, Tetrahedron, 53(10), 1997, pp. 3707-3722
N-Substituted 1,4,5,6-tetrahydropyridazines ((3) under bar) can be pre
pared in a one pot procedure from a hydrazine (1) under bar) and 2,5-d
imethoxytetrahydrofuran ((2) under bar) using NaBH4 in aqueous-THF aci
dic medium in fair yields. Variable amounts of two side products are a
lso formed: hexahydropyridazines (5) under bar, likely produced by a r
oute other than the direct reduction of (3) under bar and 1-aminopyrro
lidines (4) under bar. A direct reduction-N-reductive ethylation of (3
) under bar could be achieved in AcOH with NaBH4. (C) 1997 Published b
y Elsevier Science Ltd.