Isoindoline: Difference between revisions

{{chembox

| verifiedrevid = 382025399

| ImageSizeL1 =

| ImageSizeR1 =

| PIN = 2,3-Dihydro-1''H''-isoindole

| CASNo_Comment = <ref>[http://www.chemicalregister.com/Isoindoline/Suppliers/pid63368.htm Isoindoline]</ref>

| PubChem = 422478

| ChemSpiderID = 373951

| SMILES = c1cccc2c1CNC2

| InChI = 1/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2

| InChIKey = GWVMLCQWXVFZCN-UHFFFAOYAS

| StdInChI = 1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2

| StdInChIKey = GWVMLCQWXVFZCN-UHFFFAOYSA-N

| C = 8 | H = 9 | N = 1

'''Isoindoline''' is a [[Heterocyclic compound|heterocyclic]] [[organic compound]] with the molecular formula C₈H₉N.<ref>[http://www.chemsynthesis.com/base/chemical-structure-22914.html Isoindoline]</ref> The parent compound has a [[Bicyclic molecule|bicyclic]] structure, consisting of a six-membered [[benzene]] ring fused to a five-membered [[nitrogen]]-containing ring. The compound's structure is similar to [[indoline]] except that the [[nitrogen]] atom is in the 2 position instead of the 1 position of the five-membered ring. Isoindoline itself is not commonly encountered, but several derivatives are found in nature and some synthetic derivatives are commercially valuable drugs, e.g. [[lenalidomide]] and [[pazinaclone]].<ref>Speck Klaus; Magauer Thomas "The chemistry of isoindole natural products" Beilstein journal of organic chemistry 2013, vol. 9, pp. 2048-78. {{doi|10.3762/bjoc.9.243}}</ref>

[[File:Lenalidomide substructures.svg|thumb|left|The drug lenalidomide contains the substructure isoindoline (red)]]

==Substituted isoindolines==

1-Substituted isoindolines and isoindolinones are chiral. Isoindolylcarboxylic acid and 1,3-disubstituted isoindolines are constituents of some pharmaceuticals and natural products. Isoindolines can be prepared by 1,2-addition of a nucleophile onto a bifunctional ε-benzoiminoenoates followed by intramolecular aza-[[Michael reaction]]. Another route involves [3+2] cycloaddition of the azomethine ylides (e.g. (CH₂)₂NR) to [[quinone]] in the presence of suitable [[catalyst]]s. These methods have also been adapted to give chiral derivatives.<ref>Pandey, G.; Varkhedkar, R.; Tiwari, D (2015) Efficient Access to Enantiopure 1,3-disubstituted Isoindolines from Selective Catalytic Fragmentation of Original Desymmetrized Rigid Overbred Template, Org. Biomol. Chem., [[DOI: 10.1039/C5OB00229J]]</ref><ref>A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization [[DOI: 10.1021/ol302987h]]</ref><ref>Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines [[DOI: 10.1039/B917246G]]</ref>

<!-- Deleted image removed: [[File:Substituted isoindoline.jpg|400px|center|Approaches towards the asymmetric synthesis of 1,3-disubstituted

isoindolines.]] -->

==Related compounds==

* [[4,7-Dihydroisoindole]]

* [[Indole]]

* [[Indene]]

* [[Indoline]]

* [[Benzofuran]]

* [[Carbazole]]

* [[Carboline]]

* [[Isatin]]

* [[Methylindole (disambiguation)|Methylindole]]

* [[Oxindole]]

* [[Pyrrole]]

* [[Skatole]]

* [[Benzene]]