The 1,3-dipolar cycloaddition (1,3-DC) of the ynamide tert-butyl N-ethynyl-N-phenylcarbamate with C-carboxymethyl-N-phenylnitrilimine affords the 5-aminopyrazole as a single regioisomer. The activation of C-4 through bromination followed by catalytic coupling with a Pd catalyst yields a tetrasubstituted pyrazole. A detailed computational study fully explains the regioselectivity.
P. Blas González, J. Z. Chandanshive, M. Fochi, B. F. Bonini, A. Mazzanti, L. Bernardi, et al. (2013). Experimental and Computational Investigation of the 1,3-Dipolar Cycloaddition of the ynamide tert-butyl-ethynyl-phenyl carbamate with C-carboxymethyl-N-phenyl nitrilimine. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 36, 8108-8114 [10.1002/ejoc.201301054].
Experimental and Computational Investigation of the 1,3-Dipolar Cycloaddition of the ynamide tert-butyl-ethynyl-phenyl carbamate with C-carboxymethyl-N-phenyl nitrilimine
FOCHI, MARIAFRANCESCA;MAZZANTI, ANDREA;BERNARDI, LUCA;LOCATELLI, ERICA;CARUANA, LORENZO;COMES FRANCHINI, MAURO
2013
Abstract
The 1,3-dipolar cycloaddition (1,3-DC) of the ynamide tert-butyl N-ethynyl-N-phenylcarbamate with C-carboxymethyl-N-phenylnitrilimine affords the 5-aminopyrazole as a single regioisomer. The activation of C-4 through bromination followed by catalytic coupling with a Pd catalyst yields a tetrasubstituted pyrazole. A detailed computational study fully explains the regioselectivity.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
