New and efficient synthesis of bi- and trisubstituted indazoles

In this paper, the synthesis of bi- and trisubstituted indazoles was described. 4-Alkoxy-7-aminoprotected-indazole or 7-aminoprotected-indazole derivatives were prepared selectively using SnCl 2 in alcohol or SnCl 2 in ethyl acetate, respectively. The effects of the halogen atom in position 3 and of...

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Published inTetrahedron Vol. 61; no. 34; pp. 8218 - 8225
Main Authors Bouissane, Latifa, Kazzouli, Saïd El, Léger, Jean-Michel, Jarry, Christian, Rakib, El Mostapha, Khouili, Mostafa, Guillaumet, Gérald
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.08.2005
Elsevier
Subjects
Alcohols
Chemistry
Chemistry, Organic
Cross-coupling reaction
Indazoles
Nucleophilic addition
Physical Sciences
Science & Technology
Cross-coupling reaction
Indazoles
Alcohols
Nucleophilic addition
VICARIOUS NUCLEOPHILIC-SUBSTITUTION
BORONIC ACIDS
MILD
HYDROGEN
cross-coupling reaction
FLEXIBLE STRATEGY
alcohols
nucleophilic addition
3-IODOINDAZOLES
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Summary:In this paper, the synthesis of bi- and trisubstituted indazoles was described. 4-Alkoxy-7-aminoprotected-indazole or 7-aminoprotected-indazole derivatives were prepared selectively using SnCl 2 in alcohol or SnCl 2 in ethyl acetate, respectively. The effects of the halogen atom in position 3 and of the N-alkylation in N-1 position of 7-nitroindazoles were investigated. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.06.038