The chemistry of isoindoles

The Curtin–Hammett principle in action: 1-amino-3H-isoindole in cycloaddition reactions

“…Isoindoles are promising active biological materials 1,2 with interesting spectral properties and are the subject of study for important theoretical questions, such as: aromaticity, tautomerism [3][4][5][6][7][8] and represent the important source of the reactive compounds and synthons used for cycloaddition reactions, [9][10][11][12][13][14] the study of the organic reactions mechanisms, new rearrangements [15][16][17][18][19][20][21] and the creation of new colouring agents. [22][23][24] The most typical reaction for simple isoindole systems is the Diels-Alder reaction but previously this reaction was associated only with isoindoles prevalently in the isoindole tautomeric form.…”

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

“…2H-Isoindole is a fairly well-used heterocyclic unit in organic chemistry [164,273,274]. The isoindole core is found in natural and synthetic products with a wide range of applications in medicinal chemistry, due to their notable antibiotic and antitumor activities and other biological properties [156,158], as well as in materials [274].…”

Benzo[f]isoindole derivatives from cycloaddition reaction of 2,4-dimethylpyrimido[2,1-a]isoindole and maleimides

“…Several reactions of pyrido[2,1-a]isoindole system with different dienophiles are reported, which demonstrated that the reaction pathway depends on the dienophile and radical system [20][21][22][23][24][25][26][27][28][29][30][31][32]. Reactions of maleimides and other dienophiles with 6-methyl-6H-isoindolo[2,1-a] quinazolin-5-one [33,34] and maleimides with 1-methyl-2-R-1H- [1,2,3]triazolo[5,1-a]isoindoles as well as 1-methyl-1H-tetrazolo[5,1-a]isoindole [35] are also reported. The formation of adducts with a 7-azabenzonorbornene structure is common for the reactions of simple isoindoles with dienophiles, but new rearrangements of intermediate moieties were found.…”

“…Comprehensive reviews described the properties of isoindoles [2][3][4]. More recent monographs present annelated tricyclic isoindoles [5,6].…”