Experimental and Computational Investigation of the 1,3‐Dipolar Cycloaddition of the Ynamide tert‐Butyl N‐Ethynyl‐N‐phenylcarbamate with C‐Carboxymethyl‐N‐phenylnitrilimine

doi:10.1002/EJOC.201301054

Paper

Experimental and Computational Investigation of the 1,3‐Dipolar Cycloaddition of the Ynamide tert‐Butyl N‐Ethynyl‐N‐phenylcarbamate with C‐Carboxymethyl‐N‐phenylnitrilimine

Published Dec 1, 2013 · P. B. González, J. Chandanshive, Mariafrancesca Fochi

European Journal of Organic Chemistry

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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.

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The 1,3-dipolar cycloaddition of ynamide tert-butyl N-ethynyl-N-phenylcarbamate with C-carboxymethyl-N-phenylnitrilimine affords 5-amino pyrazole

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Experimental and Computational Investigation of the 1,3‐Dipolar Cycloaddition of the Ynamide tert‐Butyl N‐Ethynyl‐N‐phenylcarbamate with C‐Carboxymethyl‐N‐phenylnitrilimine

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