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N,N'-Di-Boc-2H-Isoindole-2-carboxamidine-First Guanidine-Substituted Isoindole.

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.

SUBMITTER: Strbac P

PROVIDER: S-EPMC9781607 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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<i>N,N</i>'-Di-Boc-2H-Isoindole-2-carboxamidine-First Guanidine-Substituted Isoindole.

Štrbac Petar P Briš Anamarija A Margetić Davor D

Molecules (Basel, Switzerland) 20221215 24

Synthesis of <i>N,N</i>'-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 reactivit ...[more]

PMID: 36558087

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