N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole

Štrbac, Petar; Briš, Anamarija; Margetić, Davor (2022) N,N′-Di-Boc-2H-Isoindole-2-carboxamidine—First Guanidine-Substituted Isoindole. Molecules, 27 (24). ISSN 1420-3049

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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.

Item Type:	Article
Uncontrolled Keywords:	cycloaddition ; Diels–Alder reaction ; heterocycles ; organic synthesis ; indoles ; DFT calculations
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Cikloadicijske strategije prema policikličkim gvanidinima Margetić, Davor IP-2018-01-3298 HRZZ
Depositing User:	Davor Margetić
Date Deposited:	03 Apr 2023 12:18
URI:	http://fulir.irb.hr/id/eprint/7823
DOI:	10.3390/molecules27248954

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