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1,3‐Dipolar Cycloaddition of Nitrile Imines with Cyclic α‐β‐Unsaturated Ketones: A Regiochemical Route to Ring‐Fused Pyrazoles
Author(s) -
Chandanshive Jay Zumbar,
Bonini Bianca Flavia,
Tiznado William,
Escobar Carlos A.,
Caballero Julio,
Femoni Cristina,
Fochi Mariafrancesca,
Comes Franchini Mauro
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100558
Subject(s) - cycloaddition , chemistry , regioselectivity , nitrile , aromatization , 1,3 dipolar cycloaddition , ring (chemistry) , reactivity (psychology) , computational chemistry , organic chemistry , medicine , alternative medicine , pathology , catalysis
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.