Mechanistic considerations on the oxime-nitrone isomerization and intramolecular cycloaddition reaction of 3-(alk-2-enylamino)propionaldehyde grimes

Authors
Noguchi, M Okada, H Tanaka, M Matsumoto, S Kakehi, A Yamamoto, H
Citation
M. Noguchi et al., Mechanistic considerations on the oxime-nitrone isomerization and intramolecular cycloaddition reaction of 3-(alk-2-enylamino)propionaldehyde grimes, B CHEM S J, 74(5), 2001, pp. 917-925
Citations number
26
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
74
Issue
5
Year of publication
2001
Pages
917 - 925
Database
ISI
SICI code
0009-2673(200105)74:5<917:MCOTOI>2.0.ZU;2-J
Abstract
3-(Alk-2-enylamino)- and 3-(acryloylamino)-2,2-dimethylpropionaldehyde oxim es underwent thermally induced 1,3-dipolar cycloaddition under mild conditi ons, leading to perhydroisoxazolo[4,3-c]pyridine derivatives. The features of the intramolecular oxime-olefin cycloaddition in this system and the rol es of the geminal methyl groups at the 2-position and the alkenylamino nitr ogen in the oxime-nitrone isomerization process are discussed based on kine tic studies.