New Trimethylaluminum-Induced Mannich-Type Reaction of Hydrazones

Trimethylaluminum addition to N-monoalkyl or N-monoaryl hydrazones followed by aldehyde addition leads to the formation of N-alkylated hydrazones in a new formal Mannich-type process. Addition compounds were also obtained in moderate yields with ketones. The mechanism as well as possible intermediat...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 68; no. 22; pp. 8733 - 8735
Main Authors El Kaim, Laurent, Grimaud, Laurence, Perroux, Yannick, Tirla, Cornelia
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.10.2003
Amer Chemical Soc
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ALUMINUM
Mannich reaction
Addition reaction
Reaction mechanism
Hydrazone
Aldehyde
Chemical synthesis
Ketone
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Summary:Trimethylaluminum addition to N-monoalkyl or N-monoaryl hydrazones followed by aldehyde addition leads to the formation of N-alkylated hydrazones in a new formal Mannich-type process. Addition compounds were also obtained in moderate yields with ketones. The mechanism as well as possible intermediates involved in the reaction are discussed.
Bibliography:istex:FD76F4E612073EBCED314BDC792FC330162EEF83
ark:/67375/TPS-NRZKH207-9
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0352272