In:
European Journal of Organic Chemistry, Wiley, Vol. 2017, No. 18 ( 2017-05-10), p. 2587-2595
Abstract:
Oxidative addition of N ‐aminophthalimide to 1,2,4‐triaryl‐1‐azabuta‐1,3‐dienes leads, in most cases, to the regiodefined formation of 1,3,5‐triarylpyrazoles in moderate to good yields through [4+1] annulation. This transformation is supposed to proceed by nitrenoid attack onto a lone pair of electrons of the imine nitrogen atom to give the vinylazomethine imine, followed by its 1,5‐electrocyclization into pyrazoline and further aromatization into pyrazole. Rare examples of 2‐imidoyl‐1‐phthalimidoaziridines that are formed by competitive [2+1] cycloaddition onto the C=C bond were isolated in low yields for 1‐azadienes with electron‐deficient aryl substituents at the imine nitrogen atom.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2017.18
DOI:
10.1002/ejoc.201700172
Language:
English
Publisher:
Wiley
Publication Date:
2017
detail.hit.zdb_id:
1475010-7
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