TY - JOUR
T1 - 1,3-dipolar cycloaddition of nitrile imines with cyclic α-β-unsaturated ketones
T2 - A regiochemical route to ring-fused pyrazoles
AU - Chandanshive, Jay Zumbar
AU - Bonini, Bianca Flavia
AU - Tiznado, William
AU - Escobar, Carlos A.
AU - Caballero, Julio
AU - Femoni, Cristina
AU - Fochi, Mariafrancesca
AU - Comes Franchini, Mauro
N1 - Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2011/9
Y1 - 2011/9
N2 - 1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with cyclic α,β-unsaturated ketones of various sizes have been studied. After cycloaddition, oxidative aromatization gives the ring-fused pyrazoles. Computational studies and the use of topological analyses of the Fukui functions allows a theoretical description of the local reactivity that is in agreement with the experimentally observed regiochemistry.
AB - 1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with cyclic α,β-unsaturated ketones of various sizes have been studied. After cycloaddition, oxidative aromatization gives the ring-fused pyrazoles. Computational studies and the use of topological analyses of the Fukui functions allows a theoretical description of the local reactivity that is in agreement with the experimentally observed regiochemistry.
KW - Computational chemistry
KW - Cycloaddition
KW - Fused-ring systems
KW - Ketones
KW - Nitrile imines
UR - http://www.scopus.com/inward/record.url?scp=80052007222&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201100558
DO - 10.1002/ejoc.201100558
M3 - Article
AN - SCOPUS:80052007222
SP - 4806
EP - 4813
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
SN - 0075-4617
IS - 25
ER -