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.
Experimental and Computational Investigation of the 1,3-Dipolar Cycloaddition of the ynamide tert-butyl-ethynyl-phenyl carbamate with C-carboxymethyl-N-phenyl nitrilimine / P. Blas González; J. Z. Chandanshive; M. Fochi; B. F. Bonini; A. Mazzanti; L. Bernardi; E. Locatelli; L. Caruana; C. Monasterolo; M. Comes Franchini.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - 36:(2013), pp. 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.
