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Experimental and Computational Investigation of the 1,3‐Dipolar Cycloaddition of the Ynamide tert ‐Butyl N ‐Ethynyl‐ N ‐phenylcarbamate with C ‐Carboxymethyl‐ N ‐phenylnitrilimine
Author(s) -
González Pedro Blas,
Chandanshive Jay Zumbar,
Fochi Mariafrancesca,
Bonini Bianca Flavia,
Mazzanti Andrea,
Bernardi Luca,
Locatelli Erica,
Caruana Lorenzo,
Monasterolo Claudio,
Comes Franchini Mauro
Publication year - 2013
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.201301054
Subject(s) - chemistry , cycloaddition , regioselectivity , pyrazole , reactivity (psychology) , halogenation , 1,3 dipolar cycloaddition , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , alternative medicine , medicine , pathology
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.