MONOSUBSTITUTED OXAZOLES - 1 - SYNTHESIS OF 5-SUBSTITUTED OXAZOLES BYDIRECTED ALKYLATION

Authors
SHAFER CM MOLINSKI TF
Citation
Cm. Shafer et Tf. Molinski, MONOSUBSTITUTED OXAZOLES - 1 - SYNTHESIS OF 5-SUBSTITUTED OXAZOLES BYDIRECTED ALKYLATION, Journal of organic chemistry, 63(3), 1998, pp. 551-555
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
3
Year of publication
1998
Pages
551 - 555
Database
ISI
SICI code
0022-3263(1998)63:3<551:MO-1-S>2.0.ZU;2-#
Abstract
A general method is presented for synthesis of 2-(methylthio)-5-substi tuted oxazoles 2. Deprotonation of the readily available 2-(methylthio )oxazole (1) with n-BuLi occurs smoothly in the presence of TMEDA and regiospecifically at C5. The organometallic la added rapidly to aldehy des and other electrophiles to provide 5-substituted-2-(methylthio)oxa zoles in very good to excellent yields. Reductive removal of the MeS g roup gave the desired 5-monosubstituted oxazoles 3 in good yield.