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Updated: Aug 16, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N,N'-Di-Boc-2H-Isoindole-2-carboxamidine-First Guanidine-Substituted Isoindole
Petar Štrbac1, Anamarija Briš1, Davor Margetić1
1Laboratory for Physical-Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, 10001 Zagreb, Croatia.
Abstract:
Synthesis of N,N'-Di-Boc-2H-isoindole-2-carboxamidine, the first representative of isoindoles containing guanidine functionality, was carried out. The cycloaddition reactivity of this new Diels-Alder heterodiene was studied and the title compound was employed as a cycloaddition delivery reagent for guanidine functionality. Higher reactivity was found in comparison with the corresponding pyrrole derivative. Substitution with fluorine or guanidine functionality does not change the reactivities of isoindoles, and these findings are in good accord with computational results.
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