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- Title
Experimental and Computational Investigation of the 1,3-Dipolar Cycloaddition of the Ynamide tert-Butyl N-Ethynyl- N-phenylcarbamate with C-Carboxymethyl- N-phenylnitrilimine.
- Authors
González, Pedro Blas; Chandanshive, Jay Zumbar; Fochi, Mariafrancesca; Bonini, Bianca Flavia; Mazzanti, Andrea; Bernardi, Luca; Locatelli, Erica; Caruana, Lorenzo; Monasterolo, Claudio; Comes Franchini, Mauro
- Abstract
The reactivity of the ynamide tert-butyl N-ethynyl- N-phenylcarbamate ( 1) in the 1,3-dipolar cycloaddition (1,3-DC) with C-carboxymethyl- N-phenylnitrilimine was investigated. This [3+2] cycloaddition affords the 5-amino pyrazole as a single regioisomer. The obtained cycloadduct has been activated at the 4-position of the pyrazole ring through bromination and subsequently coupled with a phenyl group under Pd catalysis. A detailed computational study has been performed to fully explain the complete regioselectivity observed.
- Subjects
RING formation (Chemistry); CHEMICAL reactions; NITRILIMINES; ORGANONITROGEN compounds; PYRAZOLES; HETEROCYCLIC compounds synthesis
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 36, p8108
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301054