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Tandem Synthesis of Polycyclic Isoindoles

Author:
Bornadiego, Ana, Díaz, Jesús, Marcos, Carlos F.
Source:
Journal of organic chemistry 2019 v.84 no.11 pp. 7426-7433
ISSN:
1520-6904
Subject:
aldehydes, chemical bonding, chemical structure, condensation reactions, cycloaddition reactions, dehydrogenation, organic chemistry, trapping
Abstract:
We report an easy multicomponent synthesis of polycyclic isoindoles from cyclic 1,3-dicarbonyls, aldehydes, isocyanides, and maleimides. The key step consists of the one-pot Diels–Alder trapping of a reactive 2-aminofuran intermediate, formed by a sequence of a Knoevenagel condensation and a [4+1] cycloaddition. Moreover, a further microwave-promoted dehydrogenative N–C bond forming reaction allows the straightforward synthesis of a natural product like isoindolocarbazole, validating the utility of our methodology to obtain isoindoles as useful intermediates for the synthesis of complex polycyclic molecules.
Agid:
6463961