:Isoindoline
{{chembox
| verifiedrevid = 382025399
| ImageFileL1 = Isoindoline numbering.svg
| ImageSizeL1 =
| ImageFileR1 = Isoindoline3d.png
| ImageSizeR1 =
| ImageNameR1 = 3D representation of isoindoline
| PIN = 2,3-Dihydro-1H-isoindole
| Section1 = {{Chembox Identifiers
| CASNo = 496-12-8
| CASNo_Comment = [http://www.chemicalregister.com/Isoindoline/Suppliers/pid63368.htm Isoindoline]
| 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
}}
| Section2 = {{Chembox Properties
| C = 8 | H = 9 | N = 1
}}
}}
Isoindoline is a heterocyclic organic compound with the molecular formula C8H9N.[http://www.chemsynthesis.com/base/chemical-structure-22914.html Isoindoline] The parent compound has a 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.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}}
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 catalysts. These methods have also been adapted to give chiral derivatives.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/C5OB00229JA Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization DOI: 10.1021/ol302987hAsymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines DOI: 10.1039/B917246G