A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates

Citation
Jh. Ahn et al., A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates, J ORG CHEM, 64(2), 1999, pp. 488-492
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
2
Year of publication
1999
Pages
488 - 492
Database
ISI
SICI code
0022-3263(19990122)64:2<488:ANMOSF>2.0.ZU;2-E
Abstract
1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylalumin ates to give propargylic amines in excellent yields, including unsubstitute d N,N-dialkyl propargylamines, which are difficult to obtain from Lithium a cetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dial kynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared vi a the desilylation of trimethylsilylpropargyl ethers.