1-SUBSTITUTED 1,4,5,6-TETRAHYDROPYRIDAZINES AND 1-(N-SUBSTITUTED)AMINOPYRROLIDINES FROM HYDRAZINES AND 2,5-DIMETHOXYTETRAHYDROFURAN

Citation
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
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
53
Issue
10
Year of publication
1997
Pages
3707 - 3722
Database
ISI
SICI code
0040-4020(1997)53:10<3707:11A1>2.0.ZU;2-Z
Abstract
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.