FORMATION OF 5-ALKOXY-2-AMINOOXAZOLES AND THEIR NOVEL REACTIVITY - EQUILIBRIUM WITH NITRILE YLIDE

Authors
FUKUSHIMA K LU YQ IBATA T
Citation
K. Fukushima et al., FORMATION OF 5-ALKOXY-2-AMINOOXAZOLES AND THEIR NOVEL REACTIVITY - EQUILIBRIUM WITH NITRILE YLIDE, Bulletin of the Chemical Society of Japan, 69(11), 1996, pp. 3289-3295
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
69
Issue
11
Year of publication
1996
Pages
3289 - 3295
Database
ISI
SICI code
0009-2673(1996)69:11<3289:FO5ATN>2.0.ZU;2-K
Abstract
The Rh-2(OAc)(4)-catalyzed reactions of diazoacetates with diisopropyl cyanamide gave 5-alkoxy-2-aminooxazoles. Their isolation was achieved by introduction of a bulky alkoxy group at 5-position. The 5-alkoxy-2- aminooxazole reacted with methanol to give a 1:1-adduct in a quantitat ive yield. The kinetic study indicates that this reaction proceeds in a stepwise mechanism including an equilibrium of the 5-alkoxy-2-aminoo xazole with a nitrile ylide intermediate.