N-(ALPHA-AMINOALKYL)BENZOTRIAZOLES - NOVEL NONSTABILIZED ALPHA-AMINOCARBANION SYNTHONS

Authors
KATRITZKY AR QI M FENG DM NICHOLS DA
Citation
Ar. Katritzky et al., N-(ALPHA-AMINOALKYL)BENZOTRIAZOLES - NOVEL NONSTABILIZED ALPHA-AMINOCARBANION SYNTHONS, Journal of organic chemistry, 62(12), 1997, pp. 4121-4124
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
12
Year of publication
1997
Pages
4121 - 4124
Database
ISI
SICI code
0022-3263(1997)62:12<4121:N-NNA>2.0.ZU;2-P
Abstract
C-Benzotriazole bonds were selectively transformed to give the corresp onding alpha-aminocarbanions when N-(alpha-aminoalkyl)benzotriazoles w ere reacted with either Li/LiBr or SmI2 in the presence of representat ive electrophiles. The ranges of applicability of the two reagents com plement each other, and together the two protocols provide a general r oute from readily available crystalline starting materials to a variet y of ''nonstabilized'' alpha-aminocarbanions that can be trapped in mo derate to good yields.