A new and efficient N-alkylation procedure for semicarbazides/semicarbazones derivatives

The treatment of hydrazones/hydrazides in the presence of alkyl halides in an aprotic medium brings about highly and efficient regioselective N-alkylation to produce the corresponding N-alkyl derivatives. An easy to perform and regioselective synthesis of N-alkyl hydrazones/hydrazides is described,...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 22; pp. 3919 - 3923
Main Authors Brondani, Dalci José, Moreira, Diogo Rodrigo de Magalhães, de Farias, Maria Patrícia A., Souza, Flávio Ricardo da S., Barbosa, Fábio Fernandes, Leite, Ana Cristina Lima
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.05.2007
Elsevier
Subjects
Aprotic medium
Chemistry
Chemistry, Organic
Hydrazides
Hydrazones
N-Alkylation
Physical Sciences
Science & Technology
Aprotic medium
Hydrazones
N-Alkylation
Hydrazides
CARBONATES
aprotic medium
SEMICARBAZONE DERIVATIVES
COMPLEXES
hydrazides
HYDRAZINES
SECONDARY-AMINES
hydrazones
N-alkylation
THIOSEMICARBAZIDES
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Summary:The treatment of hydrazones/hydrazides in the presence of alkyl halides in an aprotic medium brings about highly and efficient regioselective N-alkylation to produce the corresponding N-alkyl derivatives. An easy to perform and regioselective synthesis of N-alkyl hydrazones/hydrazides is described, which uses an aprotic medium with kinetic control. This procedure produced the desired monoalkylated or dialkylated amines with excellent yields and selectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.03.057